Mechanism of 2,6-Dichloro-4,4′-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical
The mechanism of 4,4′-bipyridine-catalyzed diboration of pyrazines was studied by experimental observation of the intermediates and by theoretical calculations. Intermediary radical species were detected by ESR measurement of the reactions of 2,6-dichloro-4,4′-bipyridines with bis(pinacolato)diboron...
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| Published in: | Bulletin of the Chemical Society of Japan Vol. 94; no. 7; pp. 1894 - 1902 |
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01-07-2021
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| Abstract | The mechanism of 4,4′-bipyridine-catalyzed diboration of pyrazines was studied by experimental observation of the intermediates and by theoretical calculations. Intermediary radical species were detected by ESR measurement of the reactions of 2,6-dichloro-4,4′-bipyridines with bis(pinacolato)diboron and identified by simulation. Based on these observations, radical processes involving 4,4′-bipyridine-stabilized boryl radicals were evaluated by DFT calculations combined with single-component artificial force induced reaction (SC-AFIR). The results of calculations indicate that a radical transfer process from 4,4′-bipyridine-stabilized boryl radical to pyrazine is a major pathway in the catalytic reaction. The origin of the high catalytic efficiency of 2,6-dichloro-4,4′-bipyridine is ascribed to the effect of the chlorine atom on the stability of the corresponding N,N′-diboryl-4,4′-bipyridinylidene. |
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| AbstractList | The mechanism of 4,4′-bipyridine-catalyzed diboration of pyrazines was studied by experimental observation of the intermediates and by theoretical calculations. Intermediary radical species were detected by ESR measurement of the reactions of 2,6-dichloro-4,4′-bipyridines with bis(pinacolato)diboron and identified by simulation. Based on these observations, radical processes involving 4,4′-bipyridine-stabilized boryl radicals were evaluated by DFT calculations combined with single-component artificial force induced reaction (SC-AFIR). The results of calculations indicate that a radical transfer process from 4,4′-bipyridine-stabilized boryl radical to pyrazine is a major pathway in the catalytic reaction. The origin of the high catalytic efficiency of 2,6-dichloro-4,4′-bipyridine is ascribed to the effect of the chlorine atom on the stability of the corresponding N,N′-diboryl-4,4′-bipyridinylidene. |
| Author | Tajima, Kunihiko Taketsugu, Tetsuya Ohmura, Toshimichi Murata, Yasujiro Ichino, Tomoya Maeda, Satoshi Morimasa, Yohei Suginome, Michinori Miyake, Yusuke |
| Author_xml | – sequence: 1 givenname: Toshimichi surname: Ohmura fullname: Ohmura, Toshimichi – sequence: 2 givenname: Yohei surname: Morimasa fullname: Morimasa, Yohei – sequence: 3 givenname: Tomoya surname: Ichino fullname: Ichino, Tomoya – sequence: 4 givenname: Yusuke surname: Miyake fullname: Miyake, Yusuke – sequence: 5 givenname: Yasujiro surname: Murata fullname: Murata, Yasujiro – sequence: 6 givenname: Michinori surname: Suginome fullname: Suginome, Michinori – sequence: 7 givenname: Kunihiko surname: Tajima fullname: Tajima, Kunihiko – sequence: 8 givenname: Tetsuya surname: Taketsugu fullname: Taketsugu, Tetsuya – sequence: 9 givenname: Satoshi surname: Maeda fullname: Maeda, Satoshi |
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| CitedBy_id | crossref_primary_10_1039_D2SC02096C crossref_primary_10_1039_D1CC02881B crossref_primary_10_1039_D3DT01828H |
| Cites_doi | 10.1063/1.3359469 10.1055/s-0036-1588431 10.1039/C9SC05627K 10.1021/jacs.0c04558 10.1002/anie.201906267 10.1039/C8CC06152A 10.1021/jacs.7b00823 10.1002/chem.202000412 10.1021/jacs.6b11813 10.1021/acs.chemrev.0c01236 10.1002/chem.201603979 10.1002/anie.201912564 10.1002/jcc.25106 10.1002/anie.201511917 10.1002/adsc.202001610 10.1021/jacs.5b00546 10.1021/acs.joc.0c02661 10.1063/1.2370993 10.1021/acs.joc.0c01963 10.1021/acs.orglett.7b01950 10.1039/C9OB01099H 10.1039/C8SC00008E 10.1055/a-1486-8169 10.1002/anie.201809608 10.1007/s00894-007-0233-4 10.1016/j.tet.2006.08.088 10.1021/jacs.7b04256 10.1002/ajoc.201900176 10.1002/jlac.19697240106 10.1039/c2cc34086k 10.1021/jacs.0c00409 10.1039/C7SC05225A 10.1002/anie.198000571 10.1007/s00214-007-0310-x 10.1039/D0CC07723B 10.1039/D1DT00921D 10.1021/acs.orglett.9b03419 10.1063/1.460343 10.1039/C8NJ03222J 10.1246/cl.170848 10.1515/pac-2014-0934 10.1021/jacs.7b03127 10.1039/C8SC05237A 10.1021/jacs.9b00917 10.1039/C6CS00692B 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-# |
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| DocumentTitleAlternate | Mechanism of 2,6-Dichloro-4,4′-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical |
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| Keywords | Organocatalyst Diboration Boryl radical |
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| References | 7J. Cao, G. Wang, L. Gao, X. Cheng, S. Li, Chem. Sci. 2018, 9, 3664. 10.1039/C7SC05225A29780496 24L. Gao, H. Zhang, X. Liu, G. Wang, S. Li, Dalton Trans. 2021, 50, 6982. 10.1039/D1DT00921D 3K. Oshima, T. Ohmura, M. Suginome, Chem. Commun. 2012, 48, 8571. 10.1039/c2cc34086k 17Y. Zhao, D. G. Truhlar, J. Chem. Phys. 2006, 125, 194101. 10.1063/1.237099317129083 11H. Esaki, N. Ito, S. Sakai, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2006, 62, 10954. 10.1016/j.tet.2006.08.088 13M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian 16, Revision C.01; Gaussian, Inc., Wallingford CT, 2016. 12This compound was prepared by iridium-catalyzed C–H borylation of 2,6-dichloropyridine. T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem., Int. Ed. 2002, 41, 3056. 9J.-Q. Qi, L. Jiao, J. Org. Chem. 2020, 85, 13877. 10.1021/acs.joc.0c0196333112613 6For pyridine-stabilized diorganoboryl radicals, see a) R. Köster, H. Bellut, G. Benedikt, E. Ziegler, Liebigs Ann. Chem. 1969, 724, 34. 10.1002/jlac.19697240106 b) K. Schlüter, A. Berndt, Angew. Chem., Int. Ed. Engl. 1980, 19, 57. 10.1002/anie.198000571 2a) A. Farre, K. Soares, R. A. Briggs, A. Balanta, D. M. Benoit, A. Bonet, Chem.—Eur. J. 2016, 22, 17552. 10.1002/chem.20160397927723203 b) T. Ohmura, Y. Morimasa, M. Suginome, Chem. Lett. 2017, 46, 1793. 10.1246/cl.170848 c) G. Wang, J. Cao, L. Gao, W. Chen, W. Huang, X. Cheng, S. Li, J. Am. Chem. Soc. 2017, 139, 3904. 10.1021/jacs.7b0082328212014 d) L. Candish, M. Teders, F. Glorius, J. Am. Chem. Soc. 2017, 139, 7440. 10.1021/jacs.7b0312728514176 e) D. Chen, G. Xu, Q. Zhou, L. W. Chung, W. Tang, J. Am. Chem. Soc. 2017, 139, 9767. 10.1021/jacs.7b0425628700227 f) W.-M. Cheng, R. Shang, B. Zhao, W.-L. Xing, Y. Fu, Org. Lett. 2017, 19, 4291. 10.1021/acs.orglett.7b0195028753311 g) S. Pinet, V. Liautard, M. Debiais, M. Pucheault, Synthesis 2017, 49, 4759. 10.1055/s-0036-1588431 h) J. Hu, G. Wang, S. Li, Z. Shi, Angew. Chem., Int. Ed. 2018, 57, 15227. 10.1002/anie.201809608 i) L. Gao, G. Wang, J. Cao, D. Yuan, C. Xu, X. Guo, S. Li, Chem. Commun. 2018, 54, 11534. 10.1039/C8CC06152A j) R. Xu, G.-P. Lu, C. Cai, New J. Chem. 2018, 42, 16456. 10.1039/C8NJ03222J k) Y. Morimasa, K. Kabasawa, T. Ohmura, M. Suginome, Asian J. Org. Chem. 2019, 8, 1092. 10.1002/ajoc.201900176 l) J. Cao, G. Wang, L. Gao, H. Chen, X. Liu, X. Cheng, S. Li, Chem. Sci. 2019, 10, 2767. 10.1039/C8SC05237A30996995 m) Y. Maekawa, Z. T. Ariki, M. Nambo, C. M. Crudden, Org. Biomol. Chem. 2019, 17, 7300. 10.1039/C9OB01099H31338500 n) L. Zhang, L. Jiao, J. Am. Chem. Soc. 2019, 141, 9124. 10.1021/jacs.9b0091731140798 o) H. Hosoya, L. C. M. Castro, I. Sultan, Y. Nakajima, T. Ohmura, K. Sato, H. Tsurugi, M. Suginome, K. Mashima, Org. Lett. 2019, 21, 9812. 10.1021/acs.orglett.9b0341931663767 p) J. L. Koniarczyk, J. W. Greenwood, J. V. Alegre-Requena, R. S. Paton, A. McNally, Angew. Chem., Int. Ed. 2019, 58, 14882. 10.1002/anie.201906267 q) H. Yang, L. Zhang, F.-Y. Zhou, L. Jiao, Chem. Sci. 2020, 11, 742. 10.1039/C9SC05627K r) L. Zhang, Z.-Q. Wu, L. Jiao, Angew. Chem., Int. Ed. 2020, 59, 2095. 10.1002/anie.201912564 s) Y. Ma, Y. Pang, S. Chabbra, E. J. Reijerse, A. Schnegg, J. Niski, M. Leutzsch, J. Cornella, Chem.—Eur. J. 2020, 26, 3738. 10.1002/chem.20200041231994764 t) L. Li, Z. Wu, H. Zhu, G. H. Robinson, Y. Xie, H. F. Schaefer, J. Am. Chem. Soc. 2020, 142, 6244. 10.1021/jacs.0c0040932160743 u) M. Zhou, K. Li, D. Chen, R. Xu, G. Xu, W. Tang, J. Am. Chem. Soc. 2020, 142, 10337. 10.1021/jacs.0c0455832459089 v) J. Jo, S. Kim, J.-H. Choi, W.-J. Chung, Chem. Commun. 2021, 57, 1360. 10.1039/D0CC07723B w) L. C. M. Castro, I. Sultan, K. Nishi, H. Tsurugi, K. Mashima, J. Org. Chem. 2021, 86, 3287. 10.1021/acs.joc.0c0266133555861 14For the simulated spectrum of 6c-d4• considering 10B and 37Cl, see Supporting Information. 18Y. Zhao, D. Truhlar, Theor. Chem. Acc. 2008, 120, 215. 10.1007/s00214-007-0310-x 23The substituent effect on the reaction of 3 with pyridines to form pyridine-stabilized boryl radicals has been evaluated. See ref. 7. 8a) L. Zhang, L. Jiao, J. Am. Chem. Soc. 2017, 139, 607. 10.1021/jacs.6b1181327997148 b) L. Zhang, L. Jiao, Chem. Sci. 2018, 9, 2711. 10.1039/C8SC00008E29732055 16C. Choi, R. Elber, J. Chem. Phys. 1991, 94, 751. 10.1063/1.460343 22A related calculation study on the reaction of bis(neopentylglycolato)diboron (B2nep2) has been reported by Qi and Jiao. See ref. 9. 4T. Ohmura, Y. Morimasa, M. Suginome, J. Am. Chem. Soc. 2015, 137, 2852. 10.1021/jacs.5b0054625669237 1For reviews see: a) G. Palau-Lluch, X. Sanz, E. L. Cascia, M. G. Civit, N. Miralles, A. B. Cuenca, E. Fernández, Pure Appl. Chem. 2015, 87, 181. 10.1515/pac-2014-0934 b) A. B. Cuenca, R. Shishido, H. Ito, E. Fernández, Chem. Soc. Rev. 2017, 46, 415. 10.1039/C6CS00692B27942683 c) Y.-M. Tian, X.-N. Guo, H. Braunschweig, U. Radius, T. B. Marder, Chem. Rev. 2021, 121, 3561. 10.1021/acs.chemrev.0c0123633596057 d) K. Hirano, M. Uchiyama, Adv. Synth. Catal. 2021, 363, 2340. 10.1002/adsc.202001610 e) L. C. Misal Castro, I. Sultan, H. Tsurugi, K. Mashima, Synthesis doi:10.1055/a-1486-8169. 10.1055/a-1486-8169 15J. J. P. Stewart, J. Mol. Model. 2007, 13, 1173. 10.1007/s00894-007-0233-417828561 20M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision D.01; Gaussian, Inc., Wallingford CT, 2013. 21ESR study on a partially deuterated 4-phenylpyridine-stabilized boryl radical has been reported. See ref. 8b. 5G. Wang, H. Zhang, J. Zhao, W. Li, J. Cao, C. Zhu, S. Li, Angew. Chem., Int. Ed. 2016, 55, 5985. 10.1002/anie.201511917 10S. Maeda, Y. Harabuchi, M. Takagi, K. Saita, K. Suzuki, T. Ichino, Y. Sumiya, K. Sugiyama, Y. Ono, J. Comput. Chem. 2018, 39, 233. 10.1002/jcc.2510629135034 19G. Scalmani, M. J. Frisch, J. Chem. Phys. 2010, 132, 114110. 10.1063/1.335946920331284 Scalmani (2024012104222421900_r19) 2010; 132 Hu (2024012104222421900_r2) 2018; 57 Cuenca (2024012104222421900_r1) 2017; 46 Hosoya (2024012104222421900_r2) 2019; 21 Zhou (2024012104222421900_r2) 2020; 142 Oshima (2024012104222421900_r3) 2012; 48 Jo (2024012104222421900_r2) 2021; 57 Cheng (2024012104222421900_r2) 2017; 19 Ma (2024012104222421900_r2) 2020; 26 2024012104222421900_r14 Ohmura (2024012104222421900_r4) 2015; 137 Schlüter (2024012104222421900_r6) 1980; 19 Farre (2024012104222421900_r2) 2016; 22 Misal Castro (2024012104222421900_r1) 2024012104222421900_r13 Choi (2024012104222421900_r16) 1991; 94 Castro (2024012104222421900_r2) 2021; 86 Qi (2024012104222421900_r9) 2020; 85 Cao (2024012104222421900_r2) 2019; 10 Candish (2024012104222421900_r2) 2017; 139 Zhang (2024012104222421900_r2) 2019; 141 Ishiyama (2024012104222421900_r12) 2002; 41 Wang (2024012104222421900_r2) 2017; 139 Maekawa (2024012104222421900_r2) 2019; 17 Tian (2024012104222421900_r1) 2021; 121 Koniarczyk (2024012104222421900_r2) 2019; 58 Yang (2024012104222421900_r2) 2020; 11 Wang (2024012104222421900_r5) 2016; 55 Zhao (2024012104222421900_r18) 2008; 120 Palau-Lluch (2024012104222421900_r1) 2015; 87 Cao (2024012104222421900_r7) 2018; 9 Zhang (2024012104222421900_r8) 2018; 9 Pinet (2024012104222421900_r2) 2017; 49 Esaki (2024012104222421900_r11) 2006; 62 Gao (2024012104222421900_r24) 2021; 50 Zhang (2024012104222421900_r8) 2017; 139 Morimasa (2024012104222421900_r2) 2019; 8 Hirano (2024012104222421900_r1) 2021; 363 Gao (2024012104222421900_r2) 2018; 54 Zhang (2024012104222421900_r2) 2020; 59 Stewart (2024012104222421900_r15) 2007; 13 Ohmura (2024012104222421900_r2) 2017; 46 Zhao (2024012104222421900_r17) 2006; 125 Xu (2024012104222421900_r2) 2018; 42 Li (2024012104222421900_r2) 2020; 142 2024012104222421900_r23 2024012104222421900_r21 2024012104222421900_r22 Chen (2024012104222421900_r2) 2017; 139 2024012104222421900_r20 Köster (2024012104222421900_r6) 1969; 724 Maeda (2024012104222421900_r10) 2018; 39 |
| References_xml | – volume: 132 start-page: 114110 year: 2010 ident: 2024012104222421900_r19 publication-title: J. Chem. Phys. doi: 10.1063/1.3359469 contributor: fullname: Scalmani – volume: 49 start-page: 4759 year: 2017 ident: 2024012104222421900_r2 publication-title: Synthesis doi: 10.1055/s-0036-1588431 contributor: fullname: Pinet – volume: 11 start-page: 742 year: 2020 ident: 2024012104222421900_r2 publication-title: Chem. Sci. doi: 10.1039/C9SC05627K contributor: fullname: Yang – volume: 142 start-page: 10337 year: 2020 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c04558 contributor: fullname: Zhou – volume: 58 start-page: 14882 year: 2019 ident: 2024012104222421900_r2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201906267 contributor: fullname: Koniarczyk – volume: 54 start-page: 11534 year: 2018 ident: 2024012104222421900_r2 publication-title: Chem. Commun. doi: 10.1039/C8CC06152A contributor: fullname: Gao – volume: 139 start-page: 3904 year: 2017 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b00823 contributor: fullname: Wang – volume: 26 start-page: 3738 year: 2020 ident: 2024012104222421900_r2 publication-title: Chem.—Eur. J. doi: 10.1002/chem.202000412 contributor: fullname: Ma – volume: 139 start-page: 607 year: 2017 ident: 2024012104222421900_r8 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.6b11813 contributor: fullname: Zhang – volume: 121 start-page: 3561 year: 2021 ident: 2024012104222421900_r1 publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.0c01236 contributor: fullname: Tian – ident: 2024012104222421900_r22 – volume: 22 start-page: 17552 year: 2016 ident: 2024012104222421900_r2 publication-title: Chem.—Eur. J. doi: 10.1002/chem.201603979 contributor: fullname: Farre – volume: 59 start-page: 2095 year: 2020 ident: 2024012104222421900_r2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201912564 contributor: fullname: Zhang – volume: 39 start-page: 233 year: 2018 ident: 2024012104222421900_r10 publication-title: J. Comput. Chem. doi: 10.1002/jcc.25106 contributor: fullname: Maeda – volume: 55 start-page: 5985 year: 2016 ident: 2024012104222421900_r5 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201511917 contributor: fullname: Wang – volume: 363 start-page: 2340 year: 2021 ident: 2024012104222421900_r1 publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.202001610 contributor: fullname: Hirano – volume: 137 start-page: 2852 year: 2015 ident: 2024012104222421900_r4 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b00546 contributor: fullname: Ohmura – volume: 86 start-page: 3287 year: 2021 ident: 2024012104222421900_r2 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.0c02661 contributor: fullname: Castro – volume: 125 start-page: 194101 year: 2006 ident: 2024012104222421900_r17 publication-title: J. Chem. Phys. doi: 10.1063/1.2370993 contributor: fullname: Zhao – volume: 85 start-page: 13877 year: 2020 ident: 2024012104222421900_r9 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.0c01963 contributor: fullname: Qi – volume: 19 start-page: 4291 year: 2017 ident: 2024012104222421900_r2 publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b01950 contributor: fullname: Cheng – volume: 17 start-page: 7300 year: 2019 ident: 2024012104222421900_r2 publication-title: Org. Biomol. Chem. doi: 10.1039/C9OB01099H contributor: fullname: Maekawa – ident: 2024012104222421900_r21 – ident: 2024012104222421900_r14 – volume: 9 start-page: 2711 year: 2018 ident: 2024012104222421900_r8 publication-title: Chem. Sci. doi: 10.1039/C8SC00008E contributor: fullname: Zhang – ident: 2024012104222421900_r20 – ident: 2024012104222421900_r1 publication-title: Synthesis doi: 10.1055/a-1486-8169 contributor: fullname: Misal Castro – volume: 57 start-page: 15227 year: 2018 ident: 2024012104222421900_r2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201809608 contributor: fullname: Hu – volume: 13 start-page: 1173 year: 2007 ident: 2024012104222421900_r15 publication-title: J. Mol. Model. doi: 10.1007/s00894-007-0233-4 contributor: fullname: Stewart – volume: 62 start-page: 10954 year: 2006 ident: 2024012104222421900_r11 publication-title: Tetrahedron doi: 10.1016/j.tet.2006.08.088 contributor: fullname: Esaki – volume: 139 start-page: 9767 year: 2017 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b04256 contributor: fullname: Chen – volume: 8 start-page: 1092 year: 2019 ident: 2024012104222421900_r2 publication-title: Asian J. Org. Chem. doi: 10.1002/ajoc.201900176 contributor: fullname: Morimasa – volume: 724 start-page: 34 year: 1969 ident: 2024012104222421900_r6 publication-title: Liebigs Ann. Chem. doi: 10.1002/jlac.19697240106 contributor: fullname: Köster – volume: 48 start-page: 8571 year: 2012 ident: 2024012104222421900_r3 publication-title: Chem. Commun. doi: 10.1039/c2cc34086k contributor: fullname: Oshima – volume: 142 start-page: 6244 year: 2020 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c00409 contributor: fullname: Li – volume: 9 start-page: 3664 year: 2018 ident: 2024012104222421900_r7 publication-title: Chem. Sci. doi: 10.1039/C7SC05225A contributor: fullname: Cao – volume: 19 start-page: 57 year: 1980 ident: 2024012104222421900_r6 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.198000571 contributor: fullname: Schlüter – volume: 120 start-page: 215 year: 2008 ident: 2024012104222421900_r18 publication-title: Theor. Chem. Acc. doi: 10.1007/s00214-007-0310-x contributor: fullname: Zhao – volume: 57 start-page: 1360 year: 2021 ident: 2024012104222421900_r2 publication-title: Chem. Commun. doi: 10.1039/D0CC07723B contributor: fullname: Jo – volume: 50 start-page: 6982 year: 2021 ident: 2024012104222421900_r24 publication-title: Dalton Trans. doi: 10.1039/D1DT00921D contributor: fullname: Gao – volume: 21 start-page: 9812 year: 2019 ident: 2024012104222421900_r2 publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b03419 contributor: fullname: Hosoya – volume: 94 start-page: 751 year: 1991 ident: 2024012104222421900_r16 publication-title: J. Chem. Phys. doi: 10.1063/1.460343 contributor: fullname: Choi – volume: 42 start-page: 16456 year: 2018 ident: 2024012104222421900_r2 publication-title: New J. Chem. doi: 10.1039/C8NJ03222J contributor: fullname: Xu – ident: 2024012104222421900_r13 – volume: 46 start-page: 1793 year: 2017 ident: 2024012104222421900_r2 publication-title: Chem. Lett. doi: 10.1246/cl.170848 contributor: fullname: Ohmura – volume: 87 start-page: 181 year: 2015 ident: 2024012104222421900_r1 publication-title: Pure Appl. Chem. doi: 10.1515/pac-2014-0934 contributor: fullname: Palau-Lluch – volume: 139 start-page: 7440 year: 2017 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b03127 contributor: fullname: Candish – volume: 10 start-page: 2767 year: 2019 ident: 2024012104222421900_r2 publication-title: Chem. Sci. doi: 10.1039/C8SC05237A contributor: fullname: Cao – ident: 2024012104222421900_r23 – volume: 141 start-page: 9124 year: 2019 ident: 2024012104222421900_r2 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.9b00917 contributor: fullname: Zhang – volume: 46 start-page: 415 year: 2017 ident: 2024012104222421900_r1 publication-title: Chem. Soc. Rev. doi: 10.1039/C6CS00692B contributor: fullname: Cuenca – volume: 41 start-page: 3056 year: 2002 ident: 2024012104222421900_r12 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-# contributor: fullname: Ishiyama |
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| Snippet | The mechanism of 4,4′-bipyridine-catalyzed diboration of pyrazines was studied by experimental observation of the intermediates and by theoretical... |
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| StartPage | 1894 |
| Title | Mechanism of 2,6-Dichloro-4,4′-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical |
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