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Artigos de revistas sobre o tema "Iridium-catalyzed borylation"

Autor: Grafiati

Publicado: 7 de setembro de 2024

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1

Shi, Yongjia, Qian Gao, and Senmiao Xu. "Iridium-Catalyzed Asymmetric C–H Borylation Enabled by Chiral Bidentate Boryl Ligands." Synlett 30, no. 19 (2019): 2107–12. http://dx.doi.org/10.1055/s-0039-1690225.

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Asymmetric synthesis of optically pure organoboron compounds is a topic that has received a number of attentions owing to their particular importance in synthetic chemistry and drug discovery. We herein highlight recent advances in the iridium-catalyzed C–H borylation of diarylmethylamines and cyclopropanes enabled by chiral bidentate boryl ligands.1 Introduction2 Ir-Catalyzed Asymmetric C(sp2)–H Borylation of Diarylmethylamines3 Ir-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclopropanes4 Conclusion

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2

Chattopadhyay, Buddhadeb, Mirja Md Mahamudul Hassan, Md Emdadul Hoque, Sayan Dey, Saikat Guria, and Brindaban Roy. "Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines." Synthesis 53, no. 18 (2021): 3333–42. http://dx.doi.org/10.1055/a-1506-3884.

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AbstractWe report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)]2 and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.

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3

Chotana, Ghayoor, Soneela Asghar, Tayyaba Shahzadi, et al. "Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls." Synthesis 50, no. 11 (2018): 2211–20. http://dx.doi.org/10.1055/s-0036-1591968.

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Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylation and hence rely on the presence of a directing group or pre-functionalization. In this paper, the preparation of biarylboronic esters by direct C–H borylation of biaryl substrates is reported. Sterically governed regioselectivities were observed in the borylation of appropriately substituted biaryls by using [Ir(OMe)(COD)]2 precatalyst and di-tert-butylbipyridyl ligand. The resulting biarylboronic esters were isolated in 38–98% yields. The synthesized biarylboronic esters were further successfully

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4

Pan, Zilong, Luhua Liu, Senmiao Xu, and Zhenlu Shen. "Ligand-free iridium-catalyzed regioselective C–H borylation of indoles." RSC Advances 11, no. 10 (2021): 5487–90. http://dx.doi.org/10.1039/d0ra10211c.

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5

Eastabrook, Andrew S., and Jonathan Sperry. "Iridium-Catalyzed Triborylation of 3-Substituted Indoles." Australian Journal of Chemistry 68, no. 12 (2015): 1810. http://dx.doi.org/10.1071/ch15393.

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Readily available 3-substituted indoles undergo a one-pot iridium-catalyzed triborylation at the C2, C5, and C7 sites. 1H NMR analysis indicates borylation at C2 and C7 occurs first (no monoborylated product is observed), with the third borylation occurring as a separate, distinct step that is sterically directed to C5 by a combination of the substituent at C3 and the boronate at C7. The resulting tetrasubstituted indoles possess a substitution pattern that is cumbersome to prepare using existing methods.

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6

Da Ros, Sara, Anthony Linden, Kim K. Baldridge, and Jay S. Siegel. "Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules." Organic Chemistry Frontiers 2, no. 6 (2015): 626–33. http://dx.doi.org/10.1039/c5qo00009b.

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Direct iridium-catalyzed multi-borylation provides a valuable tool for the symmetric functionalization of various polycyclic aromatic hydrocarbons, inter alia, regular fivefold derivatization of corannulene.

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7

Hitosugi, Shunpei, Yuta Nakamura, Taisuke Matsuno, Waka Nakanishi, and Hiroyuki Isobe. "Iridium-catalyzed direct borylation of phenacenes." Tetrahedron Letters 53, no. 9 (2012): 1180–82. http://dx.doi.org/10.1016/j.tetlet.2011.12.106.

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8

Chotana, Ghayoor A., Jose R. Montero Bastidas, Susanne L. Miller, Milton R. Smith, and Robert E. Maleczka. "One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes." Molecules 25, no. 7 (2020): 1754. http://dx.doi.org/10.3390/molecules25071754.

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Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.

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9

Ishiyama, Tatsuo, and Norio Miyaura. "Iridium-catalyzed borylation of arenes and heteroarenes via C-H activation." Pure and Applied Chemistry 78, no. 7 (2006): 1369–75. http://dx.doi.org/10.1351/pac200678071369.

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Direct C-H borylation of aromatic compounds catalyzed by a transition-metal complex was studied as an economical protocol for the synthesis of aromatic boron derivatives. Iridium complexes generated from Ir(I) precursors and 2,2'-bipyridine ligands efficiently catalyzed the reactions of arenes and heteroarenes with bis(pinacolato)diboron or pinacolborane to produce a variety of aryl- and heteroarylboron compounds. The catalytic cycle involves the formation of a tris(boryl)iridium(III) species and its oxidative addition to an aromatic C-H bond.

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10

Wang, Yongpeng, Mengzhu Liu, Yang Sun, et al. "Aluminium borate whiskers grafted with boric acid containing poly(ether ether ketone) as a reinforcing agent for the preparation of poly(ether ether ketone) composites." RSC Advances 5, no. 122 (2015): 100856–64. http://dx.doi.org/10.1039/c5ra19635c.

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A new soluble boron-containing poly(ether ether ketone) (B-PEEK) was synthesized through iridium-catalyzed C–H borylation and grafted on the surface of aluminum borate whiskers as the coupling agent between the whiskers and PEEK matrix.

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11

Liskey, Carl W., Xuebin Liao, and John F. Hartwig. "Cyanation of Arenes via Iridium-Catalyzed Borylation." Journal of the American Chemical Society 132, no. 33 (2010): 11389–91. http://dx.doi.org/10.1021/ja104442v.

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12

Sadler, Scott A., Hazmi Tajuddin, Ibraheem A. I. Mkhalid, et al. "Iridium-catalyzed C–H borylation of pyridines." Organic & Biomolecular Chemistry 12, no. 37 (2014): 7318. http://dx.doi.org/10.1039/c4ob01565g.

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13

Liskey, Carl W., and John F. Hartwig. "Iridium-Catalyzed C–H Borylation of Cyclopropanes." Journal of the American Chemical Society 135, no. 9 (2013): 3375–78. http://dx.doi.org/10.1021/ja400103p.

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14

Huang, Genping, Marcin Kalek, Rong-Zhen Liao, and Fahmi Himo. "Mechanism, reactivity, and selectivity of the iridium-catalyzed C(sp3)–H borylation of chlorosilanes." Chemical Science 6, no. 3 (2015): 1735–46. http://dx.doi.org/10.1039/c4sc01592d.

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DFT calculations are used to elucidate the reaction mechanism, the role of the chlorosilyl group, and primary vs. secondary and C(sp<sup>3</sup>)–H vs. C(sp<sup>2</sup>)–H selectivity of the iridium-catalyzed borylation of chlorosilanes.

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15

Liu, Yuhua, Jipei Chen, Kangsheng Zhan, Yiqiang Shen, Hui Gao, and Lingmin Yao. "Mechanistic study of the ligand controlled regioselectivity in iridium catalyzed C–H borylation of aromatic imines." RSC Advances 8, no. 62 (2018): 35453–60. http://dx.doi.org/10.1039/c8ra07886f.

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DFT calculation indicates that in iridium catalyzed C–H borylation of aromatics, the ortho selectivity is proposed to be attributed to the electron donating effect of AQ ligand, while the meta selectivity is due to steric hindrance of TMP ligand.

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16

Tobisu, Mamoru, Takuya Igarashi, and Naoto Chatani. "Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane." Beilstein Journal of Organic Chemistry 12 (April 7, 2016): 654–61. http://dx.doi.org/10.3762/bjoc.12.65.

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Catalytic C–H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C–H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the borylation of arenes and heteroarenes. The resulting aminoborylated products can be converted to the corresponding boronic acid derivatives simply by treatment with suitable diols or diamines.

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17

Hirano, Koji, Masahiro Miura, and Wataru Miura. "Iridium-Catalyzed Site-Selective C–H Borylation of 2-Pyridones." Synthesis 49, no. 21 (2017): 4745–52. http://dx.doi.org/10.1055/s-0036-1588735.

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An iridium-catalyzed site-selective C–H borylation of 2-pyridones has been developed. The site selectivity is predominantly controlled by steric factors, and we can access C4, C5, and C6 C–H on the 2-pyridone ring by the judicious choice of ligand and solvent. Subsequent Suzuki–Miyaura cross-coupling of the borylated products also proceeds to form the corresponding arylated pyridones in good overall yields.

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18

Kuleshova, Olena, Sobi Asako, and Laurean Ilies. "Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes." ACS Catalysis 11, no. 10 (2021): 5968–73. http://dx.doi.org/10.1021/acscatal.1c01206.

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19

Song, Shu-Yong, Yinwu Li, Zhuofeng Ke, and Senmiao Xu. "Iridium-Catalyzed Enantioselective C–H Borylation of Diarylphosphinates." ACS Catalysis 11, no. 21 (2021): 13445–51. http://dx.doi.org/10.1021/acscatal.1c03888.

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20

Robbins, Daniel W., Timothy A. Boebel, and John F. Hartwig. "Iridium-Catalyzed, Silyl-Directed Borylation of Nitrogen-Containing Heterocycles." Journal of the American Chemical Society 132, no. 12 (2010): 4068–69. http://dx.doi.org/10.1021/ja1006405.

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21

Liskey, Carl W., and John F. Hartwig. "ChemInform Abstract: Iridium-Catalyzed C-H Borylation of Cyclopropanes." ChemInform 44, no. 34 (2013): no. http://dx.doi.org/10.1002/chin.201334177.

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22

Steel, Patrick G., and et al et al. "ChemInform Abstract: Iridium-Catalyzed C-H Borylation of Pyridines." ChemInform 46, no. 9 (2015): no. http://dx.doi.org/10.1002/chin.201509190.

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23

Liskey, Carl W., Xuebin Liao, and John F. Hartwig. "ChemInform Abstract: Cyanation of Arenes via Iridium-Catalyzed Borylation." ChemInform 42, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.201104045.

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24

Mamlouk, Hind, Jakkrit Suriboot, Praveen Kumar Manyam, Ahmed AlYazidi, David E. Bergbreiter, and Sherzod T. Madrahimov. "Highly active, separable and recyclable bipyridine iridium catalysts for C–H borylation reactions." Catalysis Science & Technology 8, no. 1 (2018): 124–27. http://dx.doi.org/10.1039/c7cy01641g.

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Iridium complexes generated from Ir(i) precursors and PIB oligomer functionalized bpy ligands efficiently catalyzed the reaction of arenes with bis(pinacolato)diboron under mild conditions to produce a variety of arylboronate compounds.

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25

Maegawa, Yoshifumi, and Shinji Inagaki. "Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane." Dalton Transactions 44, no. 29 (2015): 13007–16. http://dx.doi.org/10.1039/c5dt00239g.

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Iridium complex fixed on periodic mesoporous organosilica containing bipyridine ligands within a framework showed efficient heterogeneous catalysis for direct C–H borylation of arenes and heteroarenes in combination with an inexpensive pinacolborane.

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26

Chotana, Ghayoor, Tayyaba Shahzadi, and Rahman Saleem. "Facile Synthesis of Halogen Decorated para-/meta-Hydroxybenzoates by Iridium-Catalyzed Borylation and Oxidation." Synthesis 50, no. 21 (2018): 4336–42. http://dx.doi.org/10.1055/s-0037-1610538.

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Hydroxybenzoates are an important class of phenols that are widely used as preservatives and antiseptics in the food and pharmaceutical industries. In this report, a facile preparation of 2,6- and 2,3-disubstituted 4/5-hydroxybenzoates by iridium-catalyzed borylation of respective disubstituted benzoate esters followed by oxidation is described. This synthetic route allows for the incorporation of halogens in the final hydroxybenzoates with substitution patterns not readily accessible by the traditional routes of aromatic functionalization.

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27

Sasaki, Ikuo, Tatsunosuke Amou, Hajime Ito, and Tatsuo Ishiyama. "Iridium-catalyzed ortho-C–H borylation of aromatic aldimines derived from pentafluoroaniline with bis(pinacolate)diboron." Org. Biomol. Chem. 12, no. 13 (2014): 2041–44. http://dx.doi.org/10.1039/c3ob42497a.

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28

Harrisson, Peter, James Morris, Todd B. Marder, and Patrick G. Steel. "Microwave-Accelerated Iridium-Catalyzed Borylation of Aromatic C−H Bonds." Organic Letters 11, no. 16 (2009): 3586–89. http://dx.doi.org/10.1021/ol901306m.

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29

Chen, Lili, Yuhuan Yang, Luhua Liu, Qian Gao та Senmiao Xu. "Iridium-Catalyzed Enantioselective α-C(sp3)–H Borylation of Azacycles". Journal of the American Chemical Society 142, № 28 (2020): 12062–68. http://dx.doi.org/10.1021/jacs.0c06756.

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30

Wang, Christy, and Jonathan Sperry. "Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones." Journal of Organic Chemistry 77, no. 6 (2012): 2584–87. http://dx.doi.org/10.1021/jo300330u.

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31

Chen, Xiang, Lili Chen, Hongliang Zhao, Qian Gao, Zhenlu Shen, and Senmiao Xu. "Iridium‐Catalyzed Enantioselective C(sp 3 )–H Borylation of Cyclobutanes." Chinese Journal of Chemistry 38, no. 12 (2020): 1533–37. http://dx.doi.org/10.1002/cjoc.202000240.

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32

Diesendruck, Charles E., Gabrielle Rubin, Jeffery A. Bertke, Danielle L. Gray, and Jeffrey S. Moore. "Crystal structure of 1,3-bis(2,3-dimethylquinoxalin-6-yl)benzene." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (2015): 1429–32. http://dx.doi.org/10.1107/s2056989015020435.

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The title compound, C26H22N4(I), was synthesized by C—H iridium-catalyzed borylation followed by Suzuki coupling. The molecular structure of (I) consists of a central benzene ring with 3-dimethylquinoxalin-6-yl groups at the 1 and 3 positions. These 2,3-dimethylquinoxalin-6-yl groups twist significantly out of the plane of the benzene ring. There are intermolecular π–π interactions which result in a two-dimensional extended structure. The layers extend parallel to theabplane and stack along thecaxis.

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33

Sperry, Jonathan, and Andrew Eastabrook. "Synthetic Access to 3,5,7-Trisubstituted Indoles Enabled by Iridium-Catalyzed C–H Borylation." Synthesis 49, no. 21 (2017): 4731–37. http://dx.doi.org/10.1055/s-0036-1589018.

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A one-pot conversion of 3-substituted indoles into their 5,7-diboryl derivatives is reported. The simultaneous functionalization of the C5-H and C7-H sites is achieved using an iridium-catalyzed triborylation-protodeborylation sequence. The 5,7-diborylindoles are useful intermediates that can be readily derivatized into a variety of indoles possessing the rare 3,5,7-trisubstitution pattern, including the natural product (+)-plakohypaphorine C.

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34

Nagase, Mai, Kenta Kato, Akiko Yagi, Yasutomo Segawa, and Kenichiro Itami. "Six-fold C–H borylation of hexa-peri-hexabenzocoronene." Beilstein Journal of Organic Chemistry 16 (March 13, 2020): 391–97. http://dx.doi.org/10.3762/bjoc.16.37.

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Hexa-peri-hexabenzocoronene (HBC) is known to be a poorly soluble polycyclic aromatic hydrocarbon for which direct functionalization methods have been very limited. Herein, the synthesis of hexaborylated HBC from unsubstituted HBC is described. Iridium-catalyzed six-fold C–H borylation of HBC was successfully achieved by screening solvents. The crystal structure of hexaborylated HBC was confirmed via X-ray crystallography. Optoelectronic properties of the thus-obtained hexaborylated HBC were analyzed with the support of density functional theory calculations. The spectra revealed a bathochromi

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35

Liu, Luhua, Rongrong Du, and Senmiao Xu. "Ligand-Free Iridium-Catalyzed Borylation of Secondary Benzylic C—H Bonds." Chinese Journal of Organic Chemistry 41, no. 4 (2021): 1572. http://dx.doi.org/10.6023/cjoc202101009.

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36

Murphy, Jaclyn M., Xuebin Liao, and John F. Hartwig. "Meta Halogenation of 1,3-Disubstituted Arenes via Iridium-Catalyzed Arene Borylation." Journal of the American Chemical Society 129, no. 50 (2007): 15434–35. http://dx.doi.org/10.1021/ja076498n.

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37

Larsen, Matthew A., Seung Hwan Cho, and John Hartwig. "Iridium-Catalyzed, Hydrosilyl-Directed Borylation of Unactivated Alkyl C–H Bonds." Journal of the American Chemical Society 138, no. 3 (2016): 762–65. http://dx.doi.org/10.1021/jacs.5b12153.

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38

Liskey, Carl W., and John F. Hartwig. "Iridium-Catalyzed Borylation of Secondary C–H Bonds in Cyclic Ethers." Journal of the American Chemical Society 134, no. 30 (2012): 12422–25. http://dx.doi.org/10.1021/ja305596v.

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39

Sadler, Scott A., Andrew C. Hones, Bryan Roberts, David Blakemore, Todd B. Marder, and Patrick G. Steel. "Multidirectional Synthesis of Substituted Indazoles via Iridium-Catalyzed C–H Borylation." Journal of Organic Chemistry 80, no. 10 (2015): 5308–14. http://dx.doi.org/10.1021/acs.joc.5b00452.

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40

Reyes, Ronald L., Tomohiro Iwai, Satoshi Maeda, and Masaya Sawamura. "Iridium-Catalyzed Asymmetric Borylation of Unactivated Methylene C(sp3)–H Bonds." Journal of the American Chemical Society 141, no. 17 (2019): 6817–21. http://dx.doi.org/10.1021/jacs.9b01952.

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41

Roering, Andrew J., Lillian V. A. Hale, Phillip A. Squier, Marissa A. Ringgold, Emily R. Wiederspan, and Timothy B. Clark. "Iridium-Catalyzed, Substrate-Directed C–H Borylation Reactions of Benzylic Amines." Organic Letters 14, no. 13 (2012): 3558–61. http://dx.doi.org/10.1021/ol301635x.

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42

Partridge, Benjamin M., and John F. Hartwig. "Sterically Controlled Iodination of Arenes via Iridium-Catalyzed C–H Borylation." Organic Letters 15, no. 1 (2012): 140–43. http://dx.doi.org/10.1021/ol303164h.

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43

Robbins, Daniel W., and John F. Hartwig. "Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation." Angewandte Chemie 125, no. 3 (2012): 967–71. http://dx.doi.org/10.1002/ange.201208203.

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44

Hume, Paul, Daniel P. Furkert, and Margaret A. Brimble. "ChemInform Abstract: Regioselective Iridium(I)-Catalyzed Remote Borylation of Oxygenated Naphthalenes." ChemInform 43, no. 42 (2012): no. http://dx.doi.org/10.1002/chin.201242094.

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45

Pang, Yadong, Tatsuo Ishiyama, Koji Kubota, and Hajime Ito. "Iridium(I)‐Catalyzed C−H Borylation in Air by Using Mechanochemistry." Chemistry – A European Journal 25, no. 18 (2019): 4654–59. http://dx.doi.org/10.1002/chem.201900685.

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46

Robbins, Daniel W., Timothy A. Boebel, and John F. Hartwig. "ChemInform Abstract: Iridium-Catalyzed, Silyl-Directed Borylation of Nitrogen-Containing Heterocycles." ChemInform 41, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.201032051.

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47

Robbins, Daniel W., and John F. Hartwig. "Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation." Angewandte Chemie International Edition 52, no. 3 (2012): 933–37. http://dx.doi.org/10.1002/anie.201208203.

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48

Kano, Haruka, Keiji Uehara, Kyohei Matsuo, Hironobu Hayashi, Hiroko Yamada, and Naoki Aratani. "Direct borylation of terrylene and quaterrylene." Beilstein Journal of Organic Chemistry 16 (April 6, 2020): 621–27. http://dx.doi.org/10.3762/bjoc.16.58.

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The preparation of large rylenes often needs the use of solubilizing groups along the rylene backbone, and all the substituents of the terrylenes and quaterrylenes were introduced before creating the rylene skeleton. In this work, we successfully synthesized 2,5,10,13-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terrylene (TB4) by using an iridium-catalyzed direct borylation of C–H bonds in terrylene in 56% yield. The product is soluble in common organic solvents and could be purified without column chromatography. Single crystal X-ray diffraction analysis revealed that the terrylene c

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49

Boebel, Timothy A., and John F. Hartwig. "Iridium-Catalyzed Preparation of Silylboranes by Silane Borylation and Their Use in the Catalytic Borylation of Arenes." Organometallics 27, no. 22 (2008): 6013–19. http://dx.doi.org/10.1021/om800696d.

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Genov, Georgi R., James L. Douthwaite, Antti S. K. Lahdenperä, David C. Gibson, and Robert J. Phipps. "Enantioselective remote C–H activation directed by a chiral cation." Science 367, no. 6483 (2020): 1246–51. http://dx.doi.org/10.1126/science.aba1120.

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Resumo:

Chiral cations have been used extensively as organocatalysts, but their application to rendering transition metal–catalyzed processes enantioselective remains rare. This is despite the success of the analogous charge-inverted strategy in which cationic metal complexes are paired with chiral anions. We report here a strategy to render a common bipyridine ligand anionic and pair its iridium complexes with a chiral cation derived from quinine. We have applied these ion-paired complexes to long-range asymmetric induction in the desymmetrization of the geminal diaryl motif, located on a carbon or p

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