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Journal articles on the topic 'Regioselective Hydroboration'

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Author: Grafiati

Published: 6 September 2023

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1

Huang, Jiuzhong, Wuxin Yan, Chaowei Tan, Wanqing Wu, and Huanfeng Jiang. "Palladium-catalyzed regioselective hydroboration of aryl alkenes with B2pin2." Chemical Communications 54, no. 14 (2018): 1770–73. http://dx.doi.org/10.1039/c7cc09432a.

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2

Liu, Tianwei, Jianghua He, and Yuetao Zhang. "Regioselective 1,2-hydroboration of N-heteroarenes using a potassium-based catalyst." Organic Chemistry Frontiers 6, no. 15 (2019): 2749–55. http://dx.doi.org/10.1039/c9qo00497a.

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3

Nichols, Brian R., Novruz G. Akhmedov, Jeffrey L. Petersen, and Brian V. Popp. "Access to a pair of ambiphilic phosphine–borane regioisomers by rhodium-catalyzed hydroboration." Dalton Transactions 47, no. 25 (2018): 8456–65. http://dx.doi.org/10.1039/c8dt01467a.

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4

Thomas, Stephen, Nate Ang, Cornelia Buettner, Scott Docherty, Alessandro Bismuto, Jonathan Carney, Jamie Docherty, and Michael Cowley. "Borane-Catalysed Hydroboration of Alkynes and Alkenes." Synthesis 50, no. 04 (November 20, 2017): 803–8. http://dx.doi.org/10.1055/s-0036-1591719.

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Simple, commercially available borane adducts, H3B·THF and H3B·SMe2, have been used to catalyse the hydroboration of alkynes and alkenes with pinacolborane to give the alkenyl and alkyl boronic esters, respectively. Alkynes and terminal alkenes underwent highly regioselective hydroboration to give the linear boronic ester products. Good functional group tolerance was observed for substrates bearing ester, amine, ether and halide substituents. This catalytic process shows comparable reactivity to transition-metal-catalysed hydroboration protocols.

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5

Reichardt, Bastian, Olaf R. Ludek, and Chris Meier. "New and Efficient Synthesis of Racemic Cyclopent-3-en-1-yl Nucleoside Analogues and Their Derivatives." Collection of Czechoslovak Chemical Communications 71, no. 7 (2006): 1011–28. http://dx.doi.org/10.1135/cccc20061011.

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A new, efficient synthesis of racemic cyclopent-3-en-1-yl nucleoside analogues has been developed starting from cyclopentadiene. The key step is the regioselective hydroboration of an intermediately formed mixture of two alkylated cyclopentadienes to give one cyclopentenol. The remaining double bond was further functionalized by hydroboration, epoxidation, cis-hydroxylation and cyclopropanation.

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6

Zhao, Jie, Zhiqiang Niu, Hua Fu, and Yadong Li. "Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency." Chem. Commun. 50, no. 16 (2014): 2058–60. http://dx.doi.org/10.1039/c3cc48670b.

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7

Yang, Ying, Jia-Hao Zeng, and Zhuang-Ping Zhan. "Regio-divergent hydroboration of terminal allenes controlled by nickel and cobalt catalysts." Organic Chemistry Frontiers 8, no. 11 (2021): 2537–42. http://dx.doi.org/10.1039/d1qo00024a.

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8

Keyzer, Evan N., Sky S. Kang, Schirin Hanf, and Dominic S. Wright. "Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation." Chemical Communications 53, no. 68 (2017): 9434–37. http://dx.doi.org/10.1039/c7cc04988a.

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9

Cao, Xu, Jia Li, Anqiao Zhu, Fan Su, Weiwei Yao, Fei Xue, and Mengtao Ma. "Syntheses of asymmetrical magnesium(i) complexes and their catalytic application in epoxide hydroboration." Organic Chemistry Frontiers 7, no. 22 (2020): 3625–32. http://dx.doi.org/10.1039/d0qo00938e.

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A series of novel structural magnesium(i) complexes stabilized by cyclopentyl and cyclohexyl substituted β-diketiminate ligands have been synthesized and used as highly active and regioselective pre-catalysts for various epoxides hydroboration.

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10

Baldassari, Lucas L., Kelvin S. Santos, Camila P. Ebersol, Diogo S. Lüdtke, and Angélica V. Moro. "Ligand-free, catalytic and regioselective hydroboration of selenoalkynes." Catalysis Science & Technology 10, no. 22 (2020): 7476–80. http://dx.doi.org/10.1039/d0cy01379j.

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11

Tai, Chia-Cheng, Ming-Shiuan Yu, Yi-Lin Chen, Wen-Hang Chuang, Ting-Hua Lin, Glenn P. A. Yap, and Tiow-Gan Ong. "Synthesis of a guanidine NHC complex and its application in borylation reactions." Chem. Commun. 50, no. 33 (2014): 4344–46. http://dx.doi.org/10.1039/c4cc00550c.

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Synthesis of guanidine-linked NHC can be achieved easily and its copper complexes were isolated and fully characterized. These Cu complexes are found to be versatile catalysts for hydroboration, semihydrogenation and carboboration of alkynes in a highly stereo- and regioselective fashion.

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12

Fan, Xiaoting, Junhao Zheng, Zhen Hua Li, and Huadong Wang. "Organoborane Catalyzed Regioselective 1,4-Hydroboration of Pyridines." Journal of the American Chemical Society 137, no. 15 (April 10, 2015): 4916–19. http://dx.doi.org/10.1021/jacs.5b03147.

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13

Kaithal, Akash, Basujit Chatterjee, and Chidambaram Gunanathan. "Ruthenium-Catalyzed Regioselective 1,4-Hydroboration of Pyridines." Organic Letters 18, no. 14 (June 28, 2016): 3402–5. http://dx.doi.org/10.1021/acs.orglett.6b01564.

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14

Zhang, Guoqi, Jing Wu, Man Wang, Haisu Zeng, Jessica Cheng, Michelle C. Neary, and Shengping Zheng. "Cobalt-Catalyzed Regioselective Hydroboration of Terminal Alkenes." European Journal of Organic Chemistry 2017, no. 38 (October 16, 2017): 5814–18. http://dx.doi.org/10.1002/ejoc.201701047.

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15

Yoshida, Hiroto, Ikuo Kageyuki, and Ken Takaki. "Silver-Catalyzed Highly Regioselective Formal Hydroboration of Alkynes." Organic Letters 16, no. 13 (June 13, 2014): 3512–15. http://dx.doi.org/10.1021/ol501465x.

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16

Endo, Kohei, Munenao Hirokami, and Takanori Shibata. "Counteranion-Accelerated RhIOAc-Catalyzed Regioselective Hydroboration of Vinylarenes." Organometallics 27, no. 20 (October 27, 2008): 5390–93. http://dx.doi.org/10.1021/om800465q.

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17

Tamang, Sem Raj, Arpita Singh, Daniel K. Unruh, and Michael Findlater. "Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes." ACS Catalysis 8, no. 7 (June 4, 2018): 6186–91. http://dx.doi.org/10.1021/acscatal.8b01166.

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18

Huang, Yun-Shuai, Jie Wang, Wan-Xin Zheng, Feng-Lian Zhang, You-Jie Yu, Min Zheng, Xiaoguo Zhou, and Yi-Feng Wang. "Regioselective radical hydroboration of electron-deficient alkenes: synthesis of α-boryl functionalized molecules." Chemical Communications 55, no. 79 (2019): 11904–7. http://dx.doi.org/10.1039/c9cc06506g.

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19

Mandal, Souvik, Piyush Kumar Verma, and K. Geetharani. "Lewis acid catalysis: regioselective hydroboration of alkynes and alkenes promoted by scandium triflate." Chemical Communications 54, no. 97 (2018): 13690–93. http://dx.doi.org/10.1039/c8cc08361d.

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20

Liu, Yuhua, ZhongJie Jiang, and Jipei Chen. "Origin of the ligand effect in the cobalt catalyzed regioselective hydroboration of 1,3-diene." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3747–53. http://dx.doi.org/10.1039/d0ob00628a.

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21

Škoch, Karel, Constantin G. Daniliuc, Gerald Kehr, and Gerhard Erker. "Using the FpXylBH2•SMe2 reagent for the regioselective synthesis of cyclic bis(alkenyl)boranes." Chemical Communications 56, no. 81 (2020): 12178–81. http://dx.doi.org/10.1039/d0cc05230b.

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22

Narasimhan, S., K. Ganeshwar Prasad, and S. Madhavan. "Remarkable regioselective hydroboration of terminal alkenes by calcium borohydride." Tetrahedron Letters 36, no. 7 (February 1995): 1141–44. http://dx.doi.org/10.1016/0040-4039(94)02441-d.

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23

Fan, Xiaoting, Junhao Zheng, Zhen Hua Li, and Huadong Wang. "ChemInform Abstract: Organoborane Catalyzed Regioselective 1,4-Hydroboration of Pyridines." ChemInform 46, no. 41 (September 24, 2015): no. http://dx.doi.org/10.1002/chin.201541209.

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24

Oliveira, Isadora M., Henrique A. Esteves, Mariana P. Darbem, Arthur Sartorelli, Thiago C. Correra, André F. Rodrigues‐Oliveira, Daniel C. Pimenta, Julio Zukerman‐Schpector, Flávia Manarin, and Hélio A. Stefani. "Stereo‐ and Regioselective Cu‐Catalyzed Hydroboration of Alkynyl Chalcogenoethers." ChemCatChem 12, no. 13 (May 25, 2020): 3545–52. http://dx.doi.org/10.1002/cctc.202000395.

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25

Ramachandran, P. Veeraraghavan, Sateesh Madhi, and Martin J. O’Donnell. "Regioselective hydroboration-oxidation and -amination of fluoro-substituted styrenes." Journal of Fluorine Chemistry 127, no. 9 (September 2006): 1252–55. http://dx.doi.org/10.1016/j.jfluchem.2006.06.013.

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26

Xi, Tuo, and Zhan Lu. "Cobalt-Catalyzed Ligand-Controlled Regioselective Hydroboration/Cyclization of 1,6-Enynes." ACS Catalysis 7, no. 2 (January 10, 2017): 1181–85. http://dx.doi.org/10.1021/acscatal.6b02816.

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27

Yao, Zi-Jian, Shibin Hong, Wei Zhang, Mengyan Liu, and Wei Deng. "Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium." Tetrahedron Letters 57, no. 8 (February 2016): 910–13. http://dx.doi.org/10.1016/j.tetlet.2016.01.049.

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28

Westcott, Stephen A., Henk P. Blom, Todd B. Marder, and R. Thomas Baker. "New homogeneous rhodium catalysts for the regioselective hydroboration of alkenes." Journal of the American Chemical Society 114, no. 23 (November 1992): 8863–69. http://dx.doi.org/10.1021/ja00049a019.

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29

Liu, Heng, Maxim Khononov, and Moris S. Eisen. "Catalytic 1,2-Regioselective Dearomatization of N-Heteroaromatics via a Hydroboration." ACS Catalysis 8, no. 4 (March 19, 2018): 3673–77. http://dx.doi.org/10.1021/acscatal.8b00074.

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30

Nawasreh, Mansour. "Chemo- and regioselective hydroboration of Δ14,15 in certain cephalostatin analogue." Chinese Chemical Letters 19, no. 12 (December 2008): 1391–94. http://dx.doi.org/10.1016/j.cclet.2008.09.055.

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31

Yoshida, Hiroto, Ikuo Kageyuki, and Ken Takaki. "ChemInform Abstract: Silver-Catalyzed Highly Regioselective Formal Hydroboration of Alkynes." ChemInform 45, no. 51 (December 4, 2014): no. http://dx.doi.org/10.1002/chin.201451049.

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32

Yoshida, Hiroto, Yuki Takemoto, and Ken Takaki. "A masked diboron in Cu-catalysed borylation reaction: highly regioselective formal hydroboration of alkynes for synthesis of branched alkenylborons." Chem. Commun. 50, no. 61 (2014): 8299–302. http://dx.doi.org/10.1039/c4cc01757a.

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Cu-catalysed α-selective formal hydroboration of alkynes by use of a masked diboron and its application to total synthesis of pharmacologically significant 1,1-disubstituted alkene derivatives are described.

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33

Xi, Yumeng, and John F. Hartwig. "Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration." Journal of the American Chemical Society 138, no. 21 (May 20, 2016): 6703–6. http://dx.doi.org/10.1021/jacs.6b02478.

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34

Oshima, Kazuyuki, Toshimichi Ohmura, and Michinori Suginome. "Regioselective Synthesis of 1,2-Dihydropyridines by Rhodium-Catalyzed Hydroboration of Pyridines." Journal of the American Chemical Society 134, no. 8 (February 17, 2012): 3699–702. http://dx.doi.org/10.1021/ja3002953.

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35

Jin, Ji-Kang, Wan-Xin Zheng, Hui-Min Xia, Feng-Lian Zhang, and Yi-Feng Wang. "Regioselective Radical Hydroboration of gem-Difluoroalkenes: Synthesis of α-Borylated Organofluorines." Organic Letters 21, no. 20 (October 9, 2019): 8414–18. http://dx.doi.org/10.1021/acs.orglett.9b03173.

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36

Park, Jin Kyoon, Brian A. Ondrusek, and D. Tyler McQuade. "Regioselective Catalytic Hydroboration of Propargylic Species Using Cu(I)-NHC Complexes." Organic Letters 14, no. 18 (September 4, 2012): 4790–93. http://dx.doi.org/10.1021/ol302086v.

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37

Zhang, Lei, Dongjie Peng, Xuebing Leng, and Zheng Huang. "Iron-Catalyzed, Atom-Economical, Chemo- and Regioselective Alkene Hydroboration with Pinacolborane." Angewandte Chemie 125, no. 13 (February 18, 2013): 3764–68. http://dx.doi.org/10.1002/ange.201210347.

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38

NARASIMHAN, S., K. G. PRASAD, and S. MADHAVAN. "ChemInform Abstract: Remarkable Regioselective Hydroboration of Terminal Alkenes by Calcium Borohydride." ChemInform 26, no. 25 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199525066.

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39

Zhang, Lei, Dongjie Peng, Xuebing Leng, and Zheng Huang. "Iron-Catalyzed, Atom-Economical, Chemo- and Regioselective Alkene Hydroboration with Pinacolborane." Angewandte Chemie International Edition 52, no. 13 (February 18, 2013): 3676–80. http://dx.doi.org/10.1002/anie.201210347.

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40

Chelvam, Venkatesh, Ramesh Reddy, and Premansh Dudhe. "Synthesis of the Deacetoxytubuvaline Fragment of Pretubulysin and its Lipophilic Analogues for Enhanced Permeability in Cancer Cell Lines." Synlett 30, no. 01 (December 6, 2018): 77–81. http://dx.doi.org/10.1055/s-0037-1611359.

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In the last two decades, tubulysins have emerged as alternatives to microtubule depolymerizing agents such as colchicine and vinblastine, which are well-established anticancer agents. However, the complex structure of tubulysins has always posed a challenge for synthetic chemists to scale up the production of these compounds. We report a new strategy for the practical gram-scale synthesis of a (4R)-4-[(tert-butoxycarbonyl)amino]-5-methylhexanoic acid through regioselective cleavage of a chiral aziridine ring with a vinyl Grignard reagent to afford tert-butyl [(1R)-1-isopropylbut-3-en-1-yl]carbamate, which was subjected to regioselective hydroboration–oxidation with 9-BBN. The resulting (4R)-4-[(tert-butoxycarbonyl)amino]-5-methylhexanoic acid was successfully transformed into the deacetoxytubuvaline fragment of pretubulysin or its highly lipophilic methyl-substituted thiazole and oxazole analogues for incorporation into pretubulysins. Increasing the lipophilicity of tubulysin or pretubulysin molecules should enhance their cell permeability and cytotoxicity in cancer cell lines.

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41

Wrackmeyer, Bernd, Elena V. Klimkina, Wolfgang Milius, Christian Butterhof, and Kathrin Inzenhofer. "1,2-Hydroboration and 1,1-Carboboration of Alkynyl(ferrocenyl)vinylsilanes. Novel Siloles." Zeitschrift für Naturforschung B 69, no. 11-12 (December 1, 2014): 1269–89. http://dx.doi.org/10.5560/znb.2014-4099.

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Abstract Alkynyl(ferrocenyl)vinylsilanes containing up to three alkynyl units were prepared and treated with 9-borabicyclo[3.3.1]nonane (9-BBN). All reactions proceeded in the beginning by regioselective 1,2-hydroboration of the vinyl group, with boron attached to the terminal carbon. This was followed by intra-molecular 1,1-carboboration, leading to fused silacarbacycles, depending on the number of C≡C bonds. Thus, new siloles and even fused siloles became available. The solution-state structures were revealed by multinuclear NMR techniques (1H, 11B, 13C, 29Si NMR), complemented by calculated single-molecule structures and calculated NMR parameters at the B3LYP/6-311+G(d,p) level of theory. In one case, the solid-state structure of a bicyclic derivative was determined.

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42

Leong, Bi-Xiang, Jiawen Lee, Yan Li, Ming-Chung Yang, Chi-Kit Siu, Ming-Der Su, and Cheuk-Wai So. "A Versatile NHC-Parent Silyliumylidene Cation for Catalytic Chemo- and Regioselective Hydroboration." Journal of the American Chemical Society 141, no. 44 (October 10, 2019): 17629–36. http://dx.doi.org/10.1021/jacs.9b06714.

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43

WESTCOTT, S. A., H. P. BLOM, T. B. MARDER, and R. T. BAKER. "ChemInform Abstract: New Homogeneous Rhodium Catalysts for the Regioselective Hydroboration of Alkenes." ChemInform 24, no. 8 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199308142.

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44

Zhu, Congjun, Jie Dong, Xueting Liu, Liuzhou Gao, Yue Zhao, Jin Xie, Shuhua Li, and Chengjian Zhu. "Photoredox‐Controlled β‐Regioselective Radical Hydroboration of Activated Alkenes with NHC‐Boranes." Angewandte Chemie 132, no. 31 (May 20, 2020): 12917–21. http://dx.doi.org/10.1002/ange.202005749.

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45

Zhu, Congjun, Jie Dong, Xueting Liu, Liuzhou Gao, Yue Zhao, Jin Xie, Shuhua Li, and Chengjian Zhu. "Photoredox‐Controlled β‐Regioselective Radical Hydroboration of Activated Alkenes with NHC‐Boranes." Angewandte Chemie International Edition 59, no. 31 (May 20, 2020): 12817–21. http://dx.doi.org/10.1002/anie.202005749.

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46

Wang, Xinxin, Yu Zhang, Dan Yuan, and Yingming Yao. "Regioselective Hydroboration and Hydrosilylation of N-Heteroarenes Catalyzed by a Zinc Alkyl Complex." Organic Letters 22, no. 14 (July 6, 2020): 5695–700. http://dx.doi.org/10.1021/acs.orglett.0c02082.

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47

Zhang, Lei, Dongjie Peng, Xuebing Leng, and Zheng Huang. "ChemInform Abstract: Iron-Catalyzed, Atom-Economical, Chemo- and Regioselective Alkene Hydroboration with Pinacolborane." ChemInform 44, no. 32 (July 18, 2013): no. http://dx.doi.org/10.1002/chin.201332193.

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48

Park, Jin Kyoon, Brian A. Ondrusek, and D. Tyler McQuade. "ChemInform Abstract: Regioselective Catalytic Hydroboration of Propargylic Species Using Cu(I)-NHC Complexes." ChemInform 44, no. 6 (February 5, 2013): no. http://dx.doi.org/10.1002/chin.201306139.

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49

Zhang, Congcong, Mi Zhou, Shiwen Liu, Bijia Wang, Zhiping Mao, Hong Xu, Yi Zhong, Linping Zhang, Bo Xu, and Xiaofeng Sui. "Copper-loaded nanocellulose sponge as a sustainable catalyst for regioselective hydroboration of alkynes." Carbohydrate Polymers 191 (July 2018): 17–24. http://dx.doi.org/10.1016/j.carbpol.2018.03.002.

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50

Oshima, Kazuyuki, Toshimichi Ohmura, and Michinori Suginome. "ChemInform Abstract: Regioselective Synthesis of 1,2-Dihydropyridines by Rhodium-Catalyzed Hydroboration of Pyridines." ChemInform 43, no. 31 (July 5, 2012): no. http://dx.doi.org/10.1002/chin.201231148.

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