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Journal articles on the topic 'Organoboron'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Wang, Honggen, Yao-Fu Zeng, Wen-Xin Lv, and Dong-Hang Tan. "Synthetic Transformations of Alkenyl MIDA Boronates toward the Efficient Construction of Organoborons." Synlett 29, no. 11 (2018): 1415–20. http://dx.doi.org/10.1055/s-0036-1591958.

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The attachment of N-methyliminodiacetyl boron (MIDA boron) to alkenes leads to a new type of activated alkenes. Synthetic manipulation of the alkene double bond while retaining the boron moiety offers an unprecedented opportunity for the construction of organoborons. These reactions feature unique reactivity, good regioselectivity, and they can be used to access organoborons that are historically difficult to prepare. Herein, we give a brief summary of advances in the use of alkenyl MIDA boronates as starting materials for organoboron synthesis. Mechanisms are discussed where relevant.

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2

Maiti, Debabrata, Sumon Basak, and Jyoti Prasad Biswas. "Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents." Synthesis 53, no. 18 (2021): 3151–79. http://dx.doi.org/10.1055/a-1485-4666.

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AbstractAryl rings are ubiquitous in the core of numerous natural product and industrially important molecules and thus their facile synthesis is of major interest in the scientific community and industry. Although multiple strategies enable access to these skeletons, metal-catalyzed C–H activation is promising due to its remarkable efficiency. Commercially available organoboron reagents, a prominent arylating partner in the cross-coupling domain, have also been utilized for direct arylation. Organoborons are bench-stable, inexpensive, and readily available coupling partners that promise regio

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3

Brown, Charles, R. Harry Cragg, Tim J. Miller, and David O'N Smith. "Organoboron compounds." Journal of Organometallic Chemistry 342, no. 2 (1988): 153–57. http://dx.doi.org/10.1016/s0022-328x(00)99452-x.

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4

Cragg, R. Harry, and Manije Nazery. "Organoboron compounds." Journal of Organometallic Chemistry 303, no. 3 (1986): 329–35. http://dx.doi.org/10.1016/0022-328x(86)82034-4.

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5

Bubnov, Yu N., A. I. Grandberg, M. Sh Grigorian, V. G. Kiselev, M. I. Struchkova, and B. M. Mikhailov. "Organoboron compounds." Journal of Organometallic Chemistry 292, no. 1-2 (1985): 93–104. http://dx.doi.org/10.1016/0022-328x(85)87325-3.

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6

Cragg, R. Harry, and Tim J. Miller. "Organoboron compounds." Journal of Organometallic Chemistry 294, no. 1 (1985): 1–6. http://dx.doi.org/10.1016/0022-328x(85)88048-7.

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7

Cragg, R. Harry, Tim J. Miller, and David O'N Smith. "Organoboron compounds." Journal of Organometallic Chemistry 302, no. 1 (1986): 19–21. http://dx.doi.org/10.1016/0022-328x(86)80058-4.

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8

Cragg, R. Harry, Tim J. Miller, and David O'N Smith. "Organoboron compounds." Journal of Organometallic Chemistry 291, no. 3 (1985): 273–75. http://dx.doi.org/10.1016/0022-328x(85)80179-0.

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9

Boldyreva, O. G., V. A. Dorokhov, and B. M. Mikhailov. "Organoboron compounds." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 2 (1985): 390–92. http://dx.doi.org/10.1007/bf00951292.

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10

Dorokhov, V. A., O. G. Boldyreva, B. M. Mikhailov, Z. A. Starikova, and I. A. Teslya. "Organoboron compounds." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 2 (1985): 393–97. http://dx.doi.org/10.1007/bf00951293.

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11

Wang, Xiaoqing, Yanping Wu, Qingsong Liu, et al. "Aggregation-induced emission (AIE) of pyridyl-enamido-based organoboron luminophores." Chemical Communications 51, no. 4 (2015): 784–87. http://dx.doi.org/10.1039/c4cc07451c.

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Organoboron complexes having aggregation-induced emission (AIE) properties are presented. A series of pyridyl-enamido-based organoboron complexes (Borepy1–4) were synthesized and the AIE behaviors of Borepy1–4 in solution and in the solid state were investigated.

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12

Kabalka, George W., Min-Liang Yao, Murthy Akula, and Li Yong. "Isotope incorporation using organoboranes." Pure and Applied Chemistry 84, no. 11 (2012): 2309–15. http://dx.doi.org/10.1351/pac-con-12-01-13.

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Isotopes have played an important role in chemistry, biology, and medicine. For the last three decades, we have focused on the use of organoboron compounds as precursors to isotopically labeled physiologically active reagents. During that period, we have successfully developed methods for incorporating short- and long-lived isotopes of carbon, nitrogen, oxygen, and the halogens using a variety of reactive organoboron precursors. In addition, labeling strategies employing polymer-supported organoboron derivatives were developed. In this report, we present a short overview focused on the evoluti

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13

Yamashita, Yohei, John C. Tellis, and Gary A. Molander. "Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis." Proceedings of the National Academy of Sciences 112, no. 39 (2015): 12026–29. http://dx.doi.org/10.1073/pnas.1509715112.

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Orthogonal reactivity modes offer substantial opportunities for rapid construction of complex small molecules. However, most strategies for imparting orthogonality to cross-coupling reactions rely on differential protection of reactive sites, greatly reducing both atom and step economies. Reported here is a strategy for orthogonal cross-coupling wherein a mechanistically distinct activation mode for transmetalation of sp3-hybridized organoboron reagents enables C-C bond formation in the presence of various protected and unprotected sp2-hybridized organoborons. This manifold has the potential f

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14

Kaiser, Peter F., Quentin I. Churches, and Craig A. Hutton. "Organoboron Reagents in the Preparation of Functionalized ?-Amino Acids." Australian Journal of Chemistry 60, no. 11 (2007): 799. http://dx.doi.org/10.1071/ch07103.

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Over the past decade, major advances in the preparation and utilization of organoboron reagents have been applied to virtually all areas of organic synthesis. The present review collates recent examples of the use of organoboron reagents in the synthesis of α-amino acids and their derivatives. Aryl- and alkenylboronic acids have been used in the asymmetric synthesis of α-amino acids through conjugate addition to unsaturated amino acids and the Petasis three-component coupling reaction. Additionally, α-amino acid derivatives with organoboron functionality on the side-chain have been prepared an

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15

Matsumoto, Fukashi, та Yoshiki Chujo. "Chiral π-conjugated organoboron polymers". Pure and Applied Chemistry 81, № 3 (2009): 433–37. http://dx.doi.org/10.1351/pac-con-08-08-01.

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A novel π-conjugated organoboron polymer with a chiral side chain was prepared by way of hydroboration polymerization between an optically active diyne monomer and triisopropylphenylborane. The achiral analog of this organoboron polymer was also prepared as reference material. Optical properties and optical activity were investigated by UV-vis absorption, fluorescence emission, and circular dichroism (CD) spectroscopy. Concentration dependence and the influence of solvent effects upon chiroptical activity are described.

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16

Pattison, Graham. "Fluorination of organoboron compounds." Organic & Biomolecular Chemistry 17, no. 23 (2019): 5651–60. http://dx.doi.org/10.1039/c9ob00832b.

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17

Kliś, Tomasz, and Marcin Kublicki. "Organoboron Compounds in Visible Light-driven Photoredox Catalysis." Current Organic Chemistry 25, no. 9 (2021): 994–1027. http://dx.doi.org/10.2174/1385272825666210225103418.

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The increasing importance of visible light photoredox catalysis as a powerful strategy for the activation of small molecules require the development of new effective radical sources and photocatalysts. The unique properties of organoboron compounds have contributed significantly to the rapid progress of photocatalysis. Since the first work on the topic in 2005, many researchers have appreciated the role of boron-containing compounds in photocatalysis, and this is reflected in several publications. In this review, we highlight the utility of organoboron compounds in various photocatalytic react

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18

Yang, Tianbao, Niu Tang, Qizhong Wan, Shuang-Feng Yin, and Renhua Qiu. "Recent Progress on Synthesis of N,N′-Chelate Organoboron Derivatives." Molecules 26, no. 5 (2021): 1401. http://dx.doi.org/10.3390/molecules26051401.

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N,N′-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, biomedical research, or other practical science. Here, we summarized the organoboron-N,N′-chelate derivatives and showed the different routes of their syntheses. Traditional methods to synthesize N,N′-chelate organoboron compounds were mainly using bidentate ligan

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19

Slutskii, V. G., M. V. Grishin, V. A. Kharitonov, A. K. Gatin, B. R. Shub, and S. A. Tsyganov. "Synthesis of organoboron nanoparticles." Russian Journal of Physical Chemistry B 7, no. 3 (2013): 343–45. http://dx.doi.org/10.1134/s1990793113030123.

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20

Qin, Yang, Cynthia Pagba, Piotr Piotrowiak, and Frieder Jäkle. "Luminescent Organoboron Quinolate Polymers." Journal of the American Chemical Society 126, no. 22 (2004): 7015–18. http://dx.doi.org/10.1021/ja039133l.

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21

Hsu, Ming-Ta S., Timothy S. Chen, and Salvatore R. Riccitiello. "Preceramic organoboron–silicon polymers." Journal of Applied Polymer Science 42, no. 3 (1991): 851–61. http://dx.doi.org/10.1002/app.1991.070420331.

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22

Nagai, Atsushi, and Yoshiki Chujo. "Luminescent Organoboron Conjugated Polymers." Chemistry Letters 39, no. 5 (2010): 430–35. http://dx.doi.org/10.1246/cl.2010.430.

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23

Jäkle, Frieder. "Lewis acidic organoboron polymers." Coordination Chemistry Reviews 250, no. 9-10 (2006): 1107–21. http://dx.doi.org/10.1016/j.ccr.2006.01.007.

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24

Qin, Yang, Guanglou Cheng, Kshitij Parab, Anand Sundararaman, and Frieder Jäkle. "Lewis acidic organoboron polymers." Macromolecular Symposia 196, no. 1 (2003): 337–45. http://dx.doi.org/10.1002/masy.200390172.

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25

Kong, Lingbing, and Chunming Cui. "Perspective on Organoboron Chemistry." Synlett 32, no. 13 (2021): 1316–22. http://dx.doi.org/10.1055/a-1405-7012.

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AbstractOrganoboron compounds play prominent roles in structural, synthetic, and materials chemistry because boron atoms can feature electrophilic, ambiphilic, or nucleophilic character. This perspective briefly describes the most recent progress in organoboron chemistry, focusing on new boron molecules and their applications that have attracted great interest from main-group chemists. The research hotspots arising from these pioneering results are also discussed.1 Introduction2 Diboron Reagents3 Boryl Anions4 Borylenes5 Nucleophilic or Ambiphilic Boron-Containing N-Heterocycles6 Conclusions a

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26

Coghi, Paolo Saul, Yinghuai Zhu, Hongming Xie, Narayan S. Hosmane, and Yingjun Zhang. "Organoboron Compounds: Effective Antibacterial and Antiparasitic Agents." Molecules 26, no. 11 (2021): 3309. http://dx.doi.org/10.3390/molecules26113309.

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The unique electron deficiency and coordination property of boron led to a wide range of applications in chemistry, energy research, materials science and the life sciences. The use of boron-containing compounds as pharmaceutical agents has a long history, and recent developments have produced encouraging strides. Boron agents have been used for both radiotherapy and chemotherapy. In radiotherapy, boron neutron capture therapy (BNCT) has been investigated to treat various types of tumors, such as glioblastoma multiforme (GBM) of brain, head and neck tumors, etc. Boron agents playing essential

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27

Lu, Xiao-Yu, Chu-Ting Yang, Jing-Hui Liu, et al. "Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds." Chemical Communications 51, no. 12 (2015): 2388–91. http://dx.doi.org/10.1039/c4cc09321f.

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28

Li, Yinghao, Zeyan Zhuang, Gengwei Lin, et al. "A new blue AIEgen based on tetraphenylethene with multiple potential applications in fluorine ion sensors, mechanochromism, and organic light-emitting diodes." New Journal of Chemistry 42, no. 6 (2018): 4089–94. http://dx.doi.org/10.1039/c7nj04742h.

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29

Lugovik, Kseniya I., Alexander K. Eltyshev, Polina O. Suntsova, et al. "Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry." Organic & Biomolecular Chemistry 16, no. 28 (2018): 5150–62. http://dx.doi.org/10.1039/c8ob00868j.

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30

Levin, Vitalij V., Alexander D. Dilman, Pavel A. Belyakov, Marina I. Struchkova, and Vladimir A. Tartakovsky. "Nucleophilic trifluoromethylation with organoboron reagents." Tetrahedron Letters 52, no. 2 (2011): 281–84. http://dx.doi.org/10.1016/j.tetlet.2010.11.025.

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31

CHUJO, YOSHIKI. "Creative Synthesis of Organoboron Polymers." NIPPON GOMU KYOKAISHI 66, no. 2 (1993): 73–79. http://dx.doi.org/10.2324/gomu.66.73.

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32

Hosoi, Kohei, Yu Kuriyama, Shinsuke Inagi, and Toshio Fuchigami. "Electrochemical hydroxylation of organoboron compounds." Chemical Communications 46, no. 8 (2010): 1284. http://dx.doi.org/10.1039/b914093j.

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33

Dhital, Raghu Nath, and Hidehiro Sakurai. "Oxidative Coupling of Organoboron Compounds." Asian Journal of Organic Chemistry 3, no. 6 (2014): 668–84. http://dx.doi.org/10.1002/ajoc.201300283.

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34

CHUJO, Y. "ChemInform Abstract: Organoboron Mainchain Polymers." ChemInform 28, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199738314.

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35

Anisimov, Anton A., Fedor V. Drozdov, Yulia S. Vysochinskaya, et al. "Organoboron Derivatives of Stereoregular Phenylcyclosilsesquioxanes." Chemistry – A European Journal 26, no. 50 (2020): 11404–7. http://dx.doi.org/10.1002/chem.202001676.

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36

Eaborn, Colin. "Organoboron Compounds in Organic Synthesis." Journal of Organometallic Chemistry 284, no. 2 (1985): C43. http://dx.doi.org/10.1016/0022-328x(85)87227-2.

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37

Petasis, Nicos A. "Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry." Australian Journal of Chemistry 60, no. 11 (2007): 795. http://dx.doi.org/10.1071/ch07360.

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The present essay offers an overview of the latest developments in the chemistry of organoboron compounds. The unique structural characteristics and the versatile reactivity profile of organoboron compounds continue to expand their roles in several areas of chemistry. A growing number of boron-mediated reactions have become vital tools for synthetic chemistry, particularly in asymmetric synthesis, metal-catalyzed processes, acid catalysis, and multicomponent reactions. As a result, boronic acids and related molecules have now evolved as major players in synthetic and medicinal chemistry. Moreo

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38

Nguyen, Viet D., Vu T. Nguyen, Shengfei Jin, Hang T. Dang, and Oleg V. Larionov. "Organoboron chemistry comes to light: Recent advances in photoinduced synthetic approaches to organoboron compounds." Tetrahedron 75, no. 5 (2019): 584–602. http://dx.doi.org/10.1016/j.tet.2018.12.040.

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39

Yamamoto, Y., E. Ohkubo, and M. Shibuya. "Selective synthesis of trisubstituted (trifluoromethyl)alkenes via ligand-free Cu-catalyzed syn hydroarylation, hydroalkenylation and hydroallylation of (trifluoromethyl)alkynes." Green Chemistry 18, no. 17 (2016): 4628–32. http://dx.doi.org/10.1039/c6gc01782g.

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40

Tsuchikawa, Masahiro, Aya Takao, Takashi Funaki, Hideki Sugihara, and Katsuhiko Ono. "Multifunctional organic dyes: anion-sensing and light-harvesting properties of curcumin boron complexes." RSC Advances 7, no. 58 (2017): 36612–16. http://dx.doi.org/10.1039/c7ra06778j.

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41

Thatikonda, Thanusha, Umed Singh, Srinivas Ambala, Ram A. Vishwakarma, and Parvinder Pal Singh. "Metal free C–H functionalization of diazines and related heteroarenes with organoboron species and its application in the synthesis of a CDK inhibitor, meriolin 1." Organic & Biomolecular Chemistry 14, no. 18 (2016): 4312–20. http://dx.doi.org/10.1039/c6ob00526h.

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42

Cain, David, Calum McLaughlin, John Molloy, Cameron Carpenter-Warren, Niall Anderson, and Allan Watson. "A Cascade Suzuki–Miyaura/Diels–Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin." Synlett 30, no. 07 (2018): 787–91. http://dx.doi.org/10.1055/s-0037-1611228.

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Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki–Miyaura/Diels–Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross-coupling and as a Diels–Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels–Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model subs

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43

Jin, Ruifa, and Wenmin Xiao. "Rational design of organoboron heteroarene derivatives as luminescent and charge transport materials for organic light-emitting diodes." New Journal of Chemistry 39, no. 10 (2015): 8188–94. http://dx.doi.org/10.1039/c5nj01499a.

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44

Chen, Jing, and Oliver S. Wenger. "Fluoride binding to an organoboron wire controls photoinduced electron transfer." Chemical Science 6, no. 6 (2015): 3582–92. http://dx.doi.org/10.1039/c5sc00964b.

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45

Liao, Chia-Wei, Rajeswara Rao M. та Shih-Sheng Sun. "Structural diversity of new solid-state luminophores based on quinoxaline-β-ketoiminate boron difluoride complexes with remarkable fluorescence switching properties". Chemical Communications 51, № 13 (2015): 2656–59. http://dx.doi.org/10.1039/c4cc08958h.

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46

Liu, Fangbin, Zicheng Ding, Jun Liu, and Lixiang Wang. "An organoboron compound with a wide absorption spectrum for solar cell applications." Chemical Communications 53, no. 90 (2017): 12213–16. http://dx.doi.org/10.1039/c7cc07494h.

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47

Valadbeigi, Younes. "Organometallic acids with azaborine, oxaborine, azaborole and oxaborole scaffolds." New Journal of Chemistry 42, no. 23 (2018): 18777–86. http://dx.doi.org/10.1039/c8nj05151h.

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48

Qi, Yanyu, Xiaosong Cao, Yang Zou, and Chuluo Yang. "Color-tunable tetracoordinated organoboron complexes exhibiting aggregation-induced emission for the efficient turn-on detection of fluoride ions." Materials Chemistry Frontiers 5, no. 5 (2021): 2353–60. http://dx.doi.org/10.1039/d1qm00046b.

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49

Qi, Yanyu, Xiaosong Cao, Yang Zou, and Chuluo Yang. "Multi-resonance organoboron-based fluorescent probe for ultra-sensitive, selective and reversible detection of fluoride ions." Journal of Materials Chemistry C 9, no. 5 (2021): 1567–71. http://dx.doi.org/10.1039/d0tc05496h.

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50

Li, Zi-Qi, Omar Apolinar, Ruohan Deng, and Keary M. Engle. "Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis." Chemical Science 12, no. 33 (2021): 11038–44. http://dx.doi.org/10.1039/d1sc03121j.

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