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Journal articles on the topic 'Decarboxylative Radical Coupling'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Niu, Pengfei, Jingya Yang, Yong Yuan, et al. "Photocatalyzed redox-neutral decarboxylative alkylation of heteroaryl methanamines." Green Chemistry 23, no. 2 (2021): 774–79. http://dx.doi.org/10.1039/d0gc04094k.

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A redox-neutral decarboxylative radical–radical coupling reaction of heteroaryl methylamines with NHPI esters has been developed by employing a copper complex as a photocatalyst with blue LED irradiation.

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2

Wu, Guibing, Jingwen Wang, Chengyu Liu та ін. "Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature". Organic Chemistry Frontiers 6, № 13 (2019): 2245–49. http://dx.doi.org/10.1039/c9qo00407f.

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3

Guo, Li-Na, Hua Wang, and Xin-Hua Duan. "Recent advances in catalytic decarboxylative acylation reactions via a radical process." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7380–91. http://dx.doi.org/10.1039/c6ob01113f.

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4

Hong, Guangfeng, Jinwei Yuan, Junhao Fu та ін. "Transition-metal-free decarboxylative C3-difluoroarylmethylation of quinoxalin-2(1H)-ones with α,α-difluoroarylacetic acids". Organic Chemistry Frontiers 6, № 8 (2019): 1173–82. http://dx.doi.org/10.1039/c9qo00105k.

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5

Zhang, Yifang, Qian Wang, Yi Peng, et al. "Metal-free, oxidative decarboxylation of aryldifluoroacetic acid with the formation of the ArS–CF2 bond." Organic & Biomolecular Chemistry 19, no. 32 (2021): 7024–30. http://dx.doi.org/10.1039/d1ob01165k.

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A metal-free, oxidative decarboxylative reaction of aryldifluoroacetic acids with disulfides or thiols under mild reaction conditions has been developed. It is an efficient radical cross-coupling method for synthesis of difluoromethylthio ethers.

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6

Pan, Shulei, Min Jiang, Jinjin Hu, Ruigang Xu, Xiaofei Zeng та Guofu Zhong. "Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived α-amino radicals to carbonyl compounds via visible-light photocatalyst in water". Green Chemistry 22, № 2 (2020): 336–41. http://dx.doi.org/10.1039/c9gc03470f.

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A general and efficient visible-light photoredox-catalyzed decarboxylative radical coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of 1,2-amino alcohols in water at room temperature is described.

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7

Fang, Zhongxue, Chenlong Wei, Jing Lin, et al. "Silver-catalyzed decarboxylative C(sp2)–C(sp3) coupling reactions via a radical mechanism." Organic & Biomolecular Chemistry 15, no. 47 (2017): 9974–78. http://dx.doi.org/10.1039/c7ob02455j.

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A silver catalyzed decarboxylative C(sp<sup>2</sup>)–C(sp<sup>3</sup>) coupling of vinylic carboxylic acids with alcohols, alkylbenzenes, cycloalkanes and cyclic ethers was developed by using DTBP as an oxidant.

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8

Zhao, Jiancan, Hong Fang, Jianlin Han, and Yi Pan. "Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process." Beilstein Journal of Organic Chemistry 9 (August 21, 2013): 1718–23. http://dx.doi.org/10.3762/bjoc.9.197.

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A Fe(acac)3-catalyzed decarboxylative coupling of 2-(aryl)vinyl carboxylic acids with cycloalkanes was developed by using DTBP as an oxidant through a radical process. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields (71–95%). The reaction also shows excellent stereoselectivity, and only trans-isomers are obtained.

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9

Yang, Hailong, Peng Sun, Yan Zhu, et al. "Copper-catalyzed decarboxylative C(sp2)–C(sp3) coupling reactions via radical mechanism." Chemical Communications 48, no. 63 (2012): 7847. http://dx.doi.org/10.1039/c2cc33203e.

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10

Wan, Zi-juan, Jin-yuan Wang, and Jun Luo. "NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers." Tetrahedron Letters 60, no. 8 (2019): 613–16. http://dx.doi.org/10.1016/j.tetlet.2019.01.039.

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11

Wang, Nai-Xing, Yalan Xing, Lei-Yang Zhang, and Yue-Hua Wu. "C(sp3)–H Bond Functionalization of Alcohols, Ketones, Nitriles, Ethers and Amides using tert-Butyl Hydroperoxide as a Radical Initiator." Synlett 32, no. 01 (2020): 23–29. http://dx.doi.org/10.1055/s-0040-1706406.

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The C(sp3)–H bond is found widely in organic molecules. Recently, the functionalization of C(sp3)–H bonds has developed into a powerful tool for augmenting highly functionalized frameworks in organic synthesis. Based on the results obtained in our group, the present account mainly summarizes recent progress on the functionalization of C(sp3)–H bonds of aliphatic alcohols, ketones, alkyl nitriles, and ethers with styrene or cinnamic acid using tert-butyl hydroperoxide (TBHP) as a radical initiator.1 Introduction2 Oxidative Coupling of Styrenes with C(sp3)–H Bonds3 Decarboxylative Cross-Coupling

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12

Manley, David W., and John C. Walton. "Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis." Beilstein Journal of Organic Chemistry 11 (September 9, 2015): 1570–82. http://dx.doi.org/10.3762/bjoc.11.173.

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Heterogeneous semiconductor photoredox catalysis (SCPC), particularly with TiO2, is evolving to provide radically new synthetic applications. In this review we describe how photoactivated SCPCs can either (i) interact with a precursor that donates an electron to the semiconductor thus generating a radical cation; or (ii) interact with an acceptor precursor that picks up an electron with production of a radical anion. The radical cations of appropriate donors convert to neutral radicals usually by loss of a proton. The most efficient donors for synthetic purposes contain adjacent functional gro

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13

Sun, Bin, Deyu Li, Xiaohui Zhuang, Rui Zhu, Aertuke Aisha, and Can Jin. "Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N-Hydroxyphthalimide Ester." Synlett 31, no. 07 (2020): 677–82. http://dx.doi.org/10.1055/s-0039-1691579.

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A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivatives. The reaction proceeds smoothly without adding any ligand, and provides the corresponding products containing a wide range of functional groups in moderate to excellent yields. This reaction uses readily available starting materials, and proceeds under mild conditions and with operational simplicity.

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14

Jin, Can, Xun Zhang, Bin Sun, Zhiyang Yan, and Tengwei Xu. "Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides." Synlett 30, no. 13 (2019): 1585–91. http://dx.doi.org/10.1055/s-0037-1611864.

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A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

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15

Jin, Can, Bin Sun, Tengwei Xu, et al. "Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis." Synlett 31, no. 04 (2020): 363–68. http://dx.doi.org/10.1055/s-0039-1691567.

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A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

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16

Zhou, Mingdong, Pitao Qin, Like Jing, Jing Sun, and Haiwu Du. "Progress in Photoinduced Decarboxylative Radical Cross-Coupling of Alkyl Carboxylic Acids and Their Derivatives." Chinese Journal of Organic Chemistry 40, no. 3 (2020): 598. http://dx.doi.org/10.6023/cjoc201909030.

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17

Tang, Lin, Lixian Wen, Tian Sun, et al. "Solvent-Controlled Copper-Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2 )−P Bond Formation." Asian Journal of Organic Chemistry 6, no. 11 (2017): 1683–92. http://dx.doi.org/10.1002/ajoc.201700434.

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18

Yang, Hailong, Peng Sun, Yan Zhu, et al. "ChemInform Abstract: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) Coupling Reactions via Radical Mechanism." ChemInform 43, no. 47 (2012): no. http://dx.doi.org/10.1002/chin.201247083.

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19

Bogonda, Ganganna, Hun Young Kim та Kyungsoo Oh. "Direct Acyl Radical Addition to 2H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids". Organic Letters 20, № 9 (2018): 2711–15. http://dx.doi.org/10.1021/acs.orglett.8b00920.

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20

Pan, Shulei, Min Jiang, Guofu Zhong, et al. "Visible-light-induced selectivity controllable synthesis of diamine or imidazoline derivatives by multicomponent decarboxylative radical coupling reactions." Organic Chemistry Frontiers 7, no. 24 (2020): 4043–49. http://dx.doi.org/10.1039/d0qo01028f.

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A visible-light-induced and photoredox-catalyzed three-component selectivity controllable synthesis of vicinal diamines and imidazoles from readily available starting materials under mild reaction conditions has been realized.

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21

Kuwana, Daiki, Yuma Komori, Masanori Nagatomo, and Masayuki Inoue. "Photoinduced Decarboxylative Radical Coupling Reaction of Multiply Oxygenated Structures by Catalysis of Pt-Doped TiO₂." Journal of Organic Chemistry 87, no. 1 (2021): 730–36. http://dx.doi.org/10.1021/acs.joc.1c02736.

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22

Jiang, Qing, Jing Jia, Bin Xu, An Zhao та Can-Cheng Guo. "Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls". Journal of Organic Chemistry 80, № 7 (2015): 3586–96. http://dx.doi.org/10.1021/acs.joc.5b00267.

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23

Jiang, Qing, Jing Jia, Bin Xu, An Zhao та Can-Cheng Guo. "ChemInform Abstract: Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling Between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls." ChemInform 46, № 33 (2015): no. http://dx.doi.org/10.1002/chin.201533101.

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24

Wang, Hui, Wenqian Fu, Lei Zhang, et al. "Basic Cu/ETS-10-N Catalyst Induced the Chemisorption and Alkyl Radical Formation of the Substrates Enhanced the Cinnamic Acid Decarboxylative Cross-Coupling Reaction Activity." Industrial & Engineering Chemistry Research 58, no. 17 (2019): 7014–24. http://dx.doi.org/10.1021/acs.iecr.9b00206.

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25

Letzel, Matthias C., Hans J. Schäfer, and Roland Fröhlich. "Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates." Beilstein Journal of Organic Chemistry 13 (January 5, 2017): 33–42. http://dx.doi.org/10.3762/bjoc.13.5.

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Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22–69% yield with a diastereoselectivity ranging from 5 to 65% de. Electrolyses without a coacid led to diastereomeric homo-coupling products in 21–50% yield with ratios of diastereomers being 1.17:2.00:0.81 to 7.03:2.00. The s

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26

Merkley, Nadine, Paul C. Venneri, and John Warkentin. "Cyclopropanation of benzylidenemalononitrile with dialkoxycarbenes and free radical rearrangement of the cyclopropanes." Canadian Journal of Chemistry 79, no. 3 (2001): 312–18. http://dx.doi.org/10.1139/v01-017.

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Thermolysis of 2-cinnamyloxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline (1a) and the analogous 2-benzyloxy-2-methoxy compound (1b) at 110°C, in benzene containing benzylidenemalononitrile, afforded products of apparent regiospecific addition of methoxycarbonyl and cinnamyl (or benzyl) radicals to the double bond. When the thermolysis of 1a was run with added TEMPO, methoxycarbonyl and cinnamyl radicals were captured. Thermolysis of the 2,2-dibenzyloxy analogue (1c) in the presence of benzylidenemalononitrile gave an adduct that is formally the product of addition of benzyloxycarbonyl and ben

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27

Merkley, Nadine, and John Warkentin. "Benzyloxy(4-substituted benzyloxy)carbenes. Generation from oxadiazolines and fragmentation to radical pairs in solution." Canadian Journal of Chemistry 78, no. 7 (2000): 942–49. http://dx.doi.org/10.1139/v00-078.

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Thermolysis of 2,2-dibenzyloxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline in benzene at 110°C leads to dibenzyloxycarbene. The carbene was trapped with tert-butyl alcohol to afford dibenzyl-tert-butyl orthoformate. In the absence of a trapping agent for the carbene, it fragmented to benzyloxycarbonyl and benzyl radicals, as shown by trapping the latter with TEMPO. In the absence of both TEMPO and tert-butyl alcohol, the radicals were partitioned between coupling to benzyl phenylacetate and decarboxylation, with subsequent formation of bibenzyl. The preferred sense of fragmentation of the analogous car

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28

Perkins, Robert J., Hai-Chao Xu, John M. Campbell, and Kevin D. Moeller. "Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones." Beilstein Journal of Organic Chemistry 9 (August 9, 2013): 1630–36. http://dx.doi.org/10.3762/bjoc.9.186.

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Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

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29

Polites, Viktor C., Shorouk O. Badir, Sebastian Keess, Anais Jolit, and Gary A. Molander. "Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor–Acceptor Complex Photoactivation." Organic Letters 23, no. 12 (2021): 4828–33. http://dx.doi.org/10.1021/acs.orglett.1c01558.

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30

Daquino, Carmelo, and Mario C. Foti. "Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes." Tetrahedron 62, no. 7 (2006): 1536–47. http://dx.doi.org/10.1016/j.tet.2005.11.010.

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31

Schäfer, Hans J., Michael Harenbrock, Elisabeth Klocke, Mark Plate, and Andreas Weiper-Idelmann. "Electrolysis for the benign conversion of renewable feedstocks." Pure and Applied Chemistry 79, no. 11 (2007): 2047–57. http://dx.doi.org/10.1351/pac200779112047.

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A large variety of C,C-bond forming reactions and functional group interconversions can be achieved by electron transfer. For the conversion of renewable feedstocks, electrolysis has been applied to coupling of radicals generated by anodic decarboxylation of fatty acids and carboxylic acids of carbohydrates. Furthermore, a derivative of L-gulonic acid is converted nearly quantitatively into L-xylonolacton. Trimethyl aconitate from trimethyl citronate is dimerized stereoselectively at the cathode in 72 % yield to a cyclic hexamethyl ester by an inter- and intramolecular Michael addition. Two ac

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32

Ortega, Pablo, Sara Gil-Guerrero, Lola González-Sánchez, Cristina Sanz-Sanz, and Pablo G. Jambrina. "Spin-Forbidden Addition of Molecular Oxygen to Stable Enol Intermediates—Decarboxylation of 2-Methyl-1-tetralone-2-carboxylic Acid." International Journal of Molecular Sciences 24, no. 8 (2023): 7424. http://dx.doi.org/10.3390/ijms24087424.

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The deprotonation of an organic substrate is a common preactivation step for the enzymatic cofactorless addition of O2 to this substrate, as it promotes charge-transfer between the two partners, inducing intersystem crossing between the triplet and singlet states involved in the process. Nevertheless, the spin-forbidden addition of O2 to uncharged ligands has also been observed in the laboratory, and the detailed mechanism of how the system circumvents the spin-forbiddenness of the reaction is still unknown. One of these examples is the cofactorless peroxidation of 2-methyl-3,4-dihydro-1-napht

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33

Mascolo, G., A. Lopez, A. Detomaso, and L. Guzzella. "UV degradation of carbofuran insecticide in aqueous solution: identification and toxicity evolution of by-products." Water Supply 4, no. 5-6 (2004): 313–19. http://dx.doi.org/10.2166/ws.2004.0122.

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The paper reports the results of an investigation about the UV degradation of carbofuran, a widely used insecticide in Europe. Specific objectives were the identification of the by-products formed and the evaluation of the toxicity of the irradiated solution compared to that of carbofuran. The experimental results, obtained treating an aqueous carbofuran solution (50 mg/L) by high pressure UV lamp (125 W), show that the insecticide is completely removed within 120 min. Several intermediate by-products have been identified by liquid chromatography-mass spectrometry (LC-MS) as a result of hydrox

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34

Mitsunuma, Harunobu, Motomu Kanai, and Yuri Katayama. "Recent Progress in Chromium-Mediated Carbonyl Addition Reactions." Synthesis 54, no. 07 (2021): 1684–94. http://dx.doi.org/10.1055/a-1696-6429.

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AbstractOrganochromium(III) species are versatile nucleophiles in complex molecule synthesis due to their high functional group tolerance and chemoselectivity for aldehydes. Traditionally, carbonyl addition reactions of organochromium(III) species were performed through reduction of organohalides either using stoichiometric chromium(II) salts or catalytic chromium salts in the presence of stoichiometric reductants [such as Mn(0)]. Recently, alternative methods emerged involving organoradical formation from readily available starting materials (e.g., N-hydroxyphthalimide esters, alkenes, and al

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35

Ren, Shi-Chao, Xing Yang, Bivas Mondal, et al. "Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones." Nature Communications 13, no. 1 (2022). http://dx.doi.org/10.1038/s41467-022-30583-2.

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AbstractThe carbene and photocatalyst co-catalyzed radical coupling of acyl electrophile and a radical precursor is emerging as attractive method for ketone synthesis. However, previous reports mainly limited to prefunctionalized radical precursors and two-component coupling. Herein, an N-heterocyclic carbene and photocatalyst catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles is disclosed, in which the carboxylic acids are directly used as radical precursors. The acyl imidazoles could also be generated in situ by reaction of a carboxylic acid with CDI thus furn

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36

Dai, Linlong, Qiaohong Zhu, Jie Zeng, et al. "Asymmetric synthesis of chiral imidazolidines by merging copper and visible light-induced photoredox catalysis." Organic Chemistry Frontiers, 2022. http://dx.doi.org/10.1039/d2qo00303a.

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A visible light induced copper catalyzed synthesis of decarboxylative radical coupling/cyclization reaction for the synthesis of chiral imidazolidines in high yields and enantioselectivities was reported.

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37

Dai, Linlong, Qiaohong Zhu, Jie Zeng, et al. "Asymmetric synthesis of chiral imidazolidines by merging copper and visible light-induced photoredox catalysis." Organic Chemistry Frontiers, 2022. http://dx.doi.org/10.1039/d2qo00303a.

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A visible light induced copper catalyzed synthesis of decarboxylative radical coupling/cyclization reaction for the synthesis of chiral imidazolidines in high yields and enantioselectivities was reported.

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38

Laudadio, Gabriele, Maximilian D. Palkowitz, Tamara El-Hayek Ewing, and Phil S. Baran. "Decarboxylative Cross-Coupling: A Radical Tool in Medicinal Chemistry." ACS Medicinal Chemistry Letters, August 10, 2022. http://dx.doi.org/10.1021/acsmedchemlett.2c00286.

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39

Song, Gui-Ting, Yuan Liu, Yong Li, et al. "Microwave-Assisted Copper Catalytic Decarboxylative Reductive Coupling of para-Quinone Methides with 3-Indoleacetic Acids: Rapid Access to Polycyclic Spiroindolequinone derivatives." Organic Chemistry Frontiers, 2023. http://dx.doi.org/10.1039/d3qo00026e.

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The green synthesis of indolylated diarylmethanes via copper-catalyzed decarboxylative reductive coupling of para-quinone methides (p-QMs) with 3-indoleacetic acids in radical reactions under microwave irradiation is described. The title compounds with...

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40

Fei, Fan, and Xianjin Yang. "Base-Promoted Radical Decarboxylative Coupling of N,N-Difluorobenzenesulfonamide and Cinnamic Acid." SSRN Electronic Journal, 2022. http://dx.doi.org/10.2139/ssrn.4200311.

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41

Fei, Fan, and Xianjin Yang. "Base-promoted radical decarboxylative coupling of N,N-Difluorobenzenesulfonamide and cinnamic acid." Tetrahedron, November 2022, 133169. http://dx.doi.org/10.1016/j.tet.2022.133169.

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42

Wang, Shuaishuai, Tingrui Li, Chengyihan Gu, et al. "Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism." Nature Communications 13, no. 1 (2022). http://dx.doi.org/10.1038/s41467-022-30176-z.

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AbstractAromatic tertiary amines are one of the most important classes of organic compounds in organic chemistry and drug discovery. It is difficult to efficiently construct tertiary amines from primary amines via classical nucleophilic substitution due to consecutive overalkylation. In this paper, we have developed a radical tandem C-N coupling strategy to efficiently construct aromatic tertiary amines from commercially available carboxylic acids and nitroarenes. A variety of aromatic tertiary amines can be furnished in good yields (up to 98%) with excellent functional group compatibility und

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43

Yu, Wing-Yiu, Chun-Ming Chan, and Yip-Chi Chow. "Recent Advances in Photocatalytic C–N Bond Coupling Reactions." Synthesis, June 3, 2020. http://dx.doi.org/10.1055/s-0040-1707136.

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Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.1 Introduction1.1 General Mechanisms for Photoredox Catalysis1.2 Pioneering

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44

Schwarz, Johanna. "Photocatalytic decarboxylations." Physical Sciences Reviews 3, no. 7 (2018). http://dx.doi.org/10.1515/psr-2017-0186.

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Abstract During the last years, the field of photocatalytic decarboxylations has emerged rapidly. Carboxylic acids are inexpensive, non-toxic and renewable starting materials for the synthesis of pharmaceuticals or platform chemicals. The traceless extrusion of CO2 gives radical intermediates, which react in diverse cross-coupling reactions. Merging photocatalysis with metal catalysis enables even broader substrate scopes or enantioselective reactions. An overview of photocatalytic decarboxylative reactions of different classes of carboxylic acids is given within this chapter.

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45

Cresswell, Alex, Joshua Dale Tibbetts, Hannah Askey, et al. "Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances." Synthesis, April 26, 2023. http://dx.doi.org/10.1055/a-2081-1830.

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The ubiquity of carboxylic acids as naturally-derived or man-made chemical feedstocks has spurred the development of powerful, decarboxylative C–C bond-forming transformations for organic synthesis. Carboxylic acids benefit not only from extensive commercial availability, but are stable surrogates for organohalides or organometallic reagents in transition metal-catalysed cross-coupling. Open shell reactivity of carboxylic acids (or derivatives thereof) to furnish carbon-centred radicals is proving transformative for synthetic chemistry, enabling novel and strategy-level C(sp3)–C bond disconnec

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46

Sun, Jie, Ziwei Li, Xiaoxiao Huang, Zhiwei Ke, and Zhiwei Chen. "Silver-catalyzed C-3 Arylthiodifluoromethylation and Aryloxydifluoromethylation of Coumarins." Organic & Biomolecular Chemistry, 2022. http://dx.doi.org/10.1039/d2ob00568a.

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A facile silver-catalyzed oxidative decarboxylation radical coupling reaction of coumarins/quinoxalin-2(1H)-ones with arylthiodifluoroacetic acids or aryloxydifluoroacetic acids were developed. This transformation provided a series of C-3 aryloxydifluoromethylated or arylthiodifluoromethylated coumarins/quinoxalin-2(1H)-ones containing...

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Shi, Yusheng, Tiexin Zhang, Xiao-Ming Jiang, Gang Xu, Cheng He, and Chunying Duan. "Synergistic photoredox and copper catalysis by diode-like coordination polymer with twisted and polar copper–dye conjugation." Nature Communications 11, no. 1 (2020). http://dx.doi.org/10.1038/s41467-020-19172-3.

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Abstract Synergistic photoredox and copper catalysis confers new synthetic possibilities in the pharmaceutical field, but is seriously affected by the consumptive fluorescence quenching of Cu(II). By decorating bulky auxiliaries into a photoreductive triphenylamine-based ligand to twist the conjugation between the triphenylamine-based ligand and the polar Cu(II)–carboxylate node in the coordination polymer, we report a heterogeneous approach to directly confront this inherent problem. The twisted and polar Cu(II)–dye conjunction endows the coordination polymer with diode-like photoelectronic b

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Xu, Qing, Linlong Dai, Zijie Wang, et al. "Renewable ultrathin carbon nitride nanosheets and its practical utilization for photocatalytic decarboxylation free radical coupling reaction." Chemical Engineering Journal, April 2023, 142990. http://dx.doi.org/10.1016/j.cej.2023.142990.

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Wang, Yanjie, Xia Meng, Changqun Cai, Lingyun Wang та Hang Gong. "Radical Cross-Coupling Reaction Based on Hydrogen Atom Abstraction of DMF and Decarboxylation of α-Ketoacid under Electricity". Journal of Organic Chemistry, 3 листопада 2022. http://dx.doi.org/10.1021/acs.joc.2c01461.

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"Mechanisms of sodium transport in bacteria." Philosophical Transactions of the Royal Society of London. B, Biological Sciences 326, no. 1236 (1990): 465–77. http://dx.doi.org/10.1098/rstb.1990.0025.

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In some bacteria, an Na + circuit is an important link between exergonic and endergonic membrane reactions. The physiological importance of Na + ion cycling is described in detail for three different bacteria. Klebsiella pneumoniae fermenting citrate pumps Na + outwards by oxaloacetate decarboxylase and uses the Na + ion gradient thus established for citrate uptake. Another possible function of the Na + gradient may be to drive the endergonic reduction of NAD + with ubiquinol as electron donor. In Vibrio alginolyticus , an Na + gradient is established by the NADH: ubiquinone oxidoreductase seg

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