Fernández, E.: 2020 Science of Synthesis, 2019/6: Advances in Organoboron Chemistry towards Organic Synthesis DOI: 10.1055/sos-SD-230-00002
Advances in Organoboron Chemistry towards Organic Synthesis

2 Mechanistic Aspects of Carbon—Boron Bond Formation

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Book

Editor: Fernández, E.

Authors: Aggarwal, V. K.; Ahmed, E.-A. M. A.; Aiken, S. G.; Bateman, J. M.; Boldrini, C.; Bose, S. K.; Carbó, J. J.; Cho, H. Y.; Clark, T. B.; Fernández, E.; Fu, Y.; Geetharani, K.; Gong, T.-J.; Ito, H.; Kitanosono, T.; Kobayashi, S.; Kubota, K.; Maseras, F.; Ohmiya, H.; Pineschi, M.; Ping, Y.; Sawamura, M.; Wang, J.; Wang, Y.-F.; Wu, C.; Xu, L.; Yoshida, H.; Zhang, F.-L.

Title: Advances in Organoboron Chemistry towards Organic Synthesis

Print ISBN: 9783132429710; Online ISBN: 9783132429758; Book DOI: 10.1055/b-006-164898

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

Mechanisms for the selective formation of carbon–boron bonds under mild reaction conditions can be better understood with the help of computational studies, either alone or in collaboration with experimental research. There is a diversity of reaction mechanisms, many of which can be effectively characterized with currently available techniques.

 
  • 1 Sameera WMC, Maseras F. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012; 2: 375
  • 2 Dang L, Lin Z, Marder TB. Chem. Commun. (Cambridge) 2009; 3987
  • 4 Cid J, Gulyás H, Carbó JJ, Fernández E. Chem. Soc. Rev. 2012; 41: 3558
  • 5 Cuenca AB, Shishido R, Ito H, Fernández E. Chem. Soc. Rev. 2017; 46: 415
  • 6 Pietsch S, Neeve EC, Apperley DC, Bertermann R, Mo F, Qiu D, Cheung MS, Dang L, Wang J, Radius U, Lin Z, Kleeberg C, Marder TB. Chem.–Eur. J. 2015; 21: 7082
  • 7 Neeve EC, Geier SJ, Mkhalid IAI, Westcott SA, Marder TB. Chem. Rev. 2016; 116: 9091
  • 8 Huang X, Lin Z, In: Computational Modeling of Homogeneous Catalysis Maseras F, Lledós A. Springer Boston 2002; 189
  • 9 Onozawa S.-y, Tanaka M. Organometallics 2001; 20: 2956
  • 10 Takahashi K, Ishiyama T, Miyaura N. Chem. Lett. 2000; 29: 982
  • 11 Zhao H, Dang L, Marder TB, Lin Z. J. Am. Chem. Soc. 2008; 130: 5586
  • 12 Cid J, Carbó JJ, Fernández E. Chem.–Eur. J. 2012; 18: 12794
  • 13 García-López D, Cid J, Marqués R, Fernández E, Carbó JJ. Chem.–Eur. J. 2017; 23: 5066
  • 14 Pubill-Ulldemolins C, Fernández E, Bo C, Brown JM. Org. Biomol. Chem. 2015; 13: 9619
  • 15 Asakawa H, Lee K.-H, Lin Z, Yamashita M. Nat. Commun. 2014; 5: 4245
  • 16 Tsukahara N, Asakawa H, Lee K.-H, Lin Z, Yamashita M. J. Am. Chem. Soc. 2017; 139: 2593
  • 17 Asakawa H, Lee K.-H, Furukawa K, Lin Z, Yamashita M. Chem.–Eur. J. 2015; 21: 4267
  • 18 Bonet A, Pubill-Ulldemolins C, Bo C, Gulyás H, Fernández E. Angew. Chem. Int. Ed. 2011; 50: 7158
  • 19 Ess DH, Wheeler SE, Iafe RG, Xu L, Çelebi-Ölçüm N, Houk KN. Angew. Chem. Int. Ed. 2008; 47: 7592
  • 20 Cuenca AB, Zigon N, Duplan V, Hoshino M, Fujita M, Fernández E. Chem.–Eur. J. 2016; 22: 4723
  • 21 Haeffner F. Comput. Theor. Chem. 2018; 1131: 90
  • 22 Fang L, Yan L, Haeffner F, Morken JP. J. Am. Chem. Soc. 2016; 138: 2508
  • 23 Yan L, Meng Y, Haeffner F, Leon RM, Crockett MP, Morken JP. J. Am. Chem. Soc. 2018; 140: 3663
  • 24 Nagashima Y, Hirano K, Takita R, Uchiyama M. J. Am. Chem. Soc. 2014; 136: 8532
  • 25 Verma A, Snead RF, Dai Y, Slebodnick C, Yang Y, Yu H, Yao F, Santos WL. Angew. Chem. Int. Ed. 2017; 56: 5111
  • 26 Civit MG, Sanz X, Vogels CM, Bo C, Westcott SA, Fernández E. Adv. Synth. Catal. 2015; 357: 3098
  • 27 García-López D, Civit MG, Vogels CM, Ricart JM, Westcott SA, Fernández E, Carbó JJ. Catal. Sci. Technol. 2018; 8: 3617
  • 28 Pubill-Ulldemolins C, Bonet A, Gulyás H, Bo C, Fernández E. Org. Biomol. Chem. 2012; 10: 9677
  • 29 Cuenca AB, Cid J, García-López D, Carbó JJ, Fernández E. Org. Biomol. Chem. 2015; 13: 9659
  • 30 Hata T, Kitagawa H, Masai H, Kurahashi T, Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2001; 40: 790
  • 31 Ohmura T, Morimasa Y, Suginome M. J. Am. Chem. Soc. 2015; 137: 2852
  • 32 Wang G, Zhang H, Zhao J, Li W, Cao J, Zhu C, Li S. Angew. Chem. Int. Ed. 2016; 55: 5985
  • 33 Pubill-Ulldemolins C, Bonet A, Bo C, Gulyás H, Fernández E. Chem.–Eur. J. 2012; 18: 1121
  • 34 Miralles N, Cid J, Cuenca AB, Carbó JJ, Fernández E. Chem. Commun. (Cambridge) 2015; 51: 1693
  • 35 García L, Sendra J, Miralles N, Reyes E, Carbó JJ, Vicario JL, Fernández E. Chem.–Eur. J. 2018; 24: 14059
  • 36 Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E. Org. Lett. 2019; 21: 2251
  • 37 Wu H, Garcia JM, Haeffner F, Radomkit S, Zhugralin AR, Hoveyda AH. J. Am. Chem. Soc. 2015; 137: 10585
  • 38 Cid J, Carbó JJ, Fernández E. Chem.–Eur. J. 2014; 20: 3616
  • 39 Wagner M, van Eikema Hommes NJR, Nöth H, Schleyer PvR. Inorg. Chem. 1995; 34: 607
  • 40 Segawa Y, Yamashita M, Nozaki K. Science (Washington, D. C.) 2006; 314: 113
  • 41 Yamashita M, Suzuki Y, Segawa Y, Nozaki K. J. Am. Chem. Soc. 2007; 129: 9570
  • 42 Segawa Y, Suzuki Y, Yamashita M, Nozaki K. J. Am. Chem. Soc. 2008; 130: 16069
  • 43 Cheung MS, Marder TB, Lin Z. Organometallics 2011; 30: 3018
  • 44 Kojima K, Nagashima Y, Wang C, Uchiyama M. ChemPlusChem 2019; 84: 277
  • 45 Ito H, Horita Y, Yamamoto E. Chem. Commun. (Cambridge) 2012; 48: 8006
  • 46 Uematsu R, Yamamoto E, Maeda S, Ito H, Taketsugu T. J. Am. Chem. Soc. 2015; 137: 4090
  • 47 Ma G, Song G, Li ZH. Phys. Chem. Chem. Phys. 2017; 19: 28313
  • 48 Geier SJ, LaFortune JHW, Zhu D, Kosnik SC, Macdonald CLB, Stephan DW, Westcott SA. Dalton Trans. 2017; 46: 10876
  • 49 Solé C, Fernández E. Angew. Chem. Int. Ed. 2013; 52: 11351
  • 50 Daley EN, Vogels CM, Geier SJ, Decken A, Doherty S, Westcott SA. Angew. Chem. Int. Ed. 2015; 54: 2121
  • 51 Geier SJ, Gilbert TM, Stephan DW. J. Am. Chem. Soc. 2008; 130: 12632
  • 52 Civit MG, Sanz X, Vogels CM, Webb JD, Geier SJ, Decken A, Bo C, Westcott SA, Fernández E. J. Org. Chem. 2015; 80: 2148
  • 53 Sanz X, Vogels CM, Decken A, Bo C, Westcott SA, Fernández E. Chem. Commun. (Cambridge) 2014; 50: 8420
  • 54 Musaev DG, Mebel AM, Morokuma K. J. Am. Chem. Soc. 1994; 116: 10693
  • 55 Dorigo AE, Schleyer PvR. Angew. Chem. Int. Ed. Engl. 1995; 34: 115
  • 56 Widauer C, Grützmacher H, Ziegler T. Organometallics 2000; 19: 2097
  • 57 Liu D, Lin Z. Organometallics 2002; 21: 4750
  • 59 Moon JH, Jung H.-Y, Lee YJ, Lee SW, Yun J, Lee JY. Organometallics 2015; 34: 2151
  • 60 Royes J, Ni S, Farré A, La Cascia E, Carbó JJ, Cuenca AB, Maseras F, Fernández E. ACS Catal. 2018; 8: 2833
  • 61 Segarra AM, Daura-Oller E, Claver C, Poblet JM, Bo C, Fernández E. Chem.–Eur. J. 2004; 10: 6456
  • 62 Daura-Oller E, Segarra AM, Poblet JM, Claver C, Fernández E, Bo C. J. Org. Chem. 2004; 69: 2669
  • 63 Yang Z.-D, Pal R, Hoang GL, Zeng XC, Takacs JM. ACS Catal. 2014; 4: 763
  • 64 Cid J, Carbó JJ, Fernández E. Chem.–Eur. J. 2012; 18: 1512
  • 65 Song L.-J, Wang T, Zhang X, Chung LW, Wu Y.-D. ACS Catal. 2017; 7: 1361
  • 66 Yang Y, Jiang J, Yu H, Shi J. Chem.–Eur. J. 2018; 24: 178
  • 67 Isegawa M, Sameera WMC, Sharma AK, Kitanosono T, Kato M, Kobayashi S, Morokuma K. ACS Catal. 2017; 7: 5370
  • 68 Lin S, Lin Z. Organometallics 2019; 38: 240
  • 69 Lv X, Wu Y.-B, Lu G. Catal. Sci. Technol. 2017; 7: 5049
  • 70 Cui Q, Musaev DG, Morokuma K. Organometallics 1997; 16: 1355
  • 71 Cui Q, Musaev DG, Morokuma K. Organometallics 1998; 17: 742
  • 72 Cui Q, Musaev DG, Morokuma K. Organometallics 1998; 17: 1383
  • 73 Sakaki S, Kikuno T. Inorg. Chem. 1997; 36: 226
  • 74 Wang M, Cheng L, Wu Z. Organometallics 2008; 27: 6464
  • 75 Liu B, Gao M, Dang L, Zhao H, Marder TB, Lin Z. Organometallics 2012; 31: 3410
  • 76 Coombs JR, Haeffner F, Kliman LT, Morken JP. J. Am. Chem. Soc. 2013; 135: 11222
  • 77 Ansell MB, Menezes da Silva VH, Heerdt G, Braga AAC, Spencer J, Navarro O. Catal. Sci. Technol. 2016; 6: 7461
  • 78 Lillo V, Mas-Marzá E, Segarra AM, Carbó JJ, Bo C, Peris E, Fernández E. Chem. Commun. (Cambridge) 2007; 3380
  • 79 Ananikov VP, Szilagyi R, Morokuma K, Musaev DG. Organometallics 2005; 24: 1938
  • 80 Pubill-Ulldemolins C, Poyatos M, Bo C, Fernández E. Dalton Trans. 2013; 42: 746
  • 81 Lillo V, Fructos MR, Ramírez J, Braga AAC, Maseras F, Díaz-Requejo MM, Pérez PJ, Fernández E. Chem.–Eur. J. 2007; 13: 2614
  • 82 Dang L, Zhao H, Lin Z, Marder TB. Organometallics 2007; 26: 2824
  • 83 Nakagawa N, Hatakeyama T, Nakamura M. Chem.–Eur. J. 2015; 21: 4257
  • 84 Dang L, Zhao H, Lin Z, Marder TB. Organometallics 2008; 27: 1178
  • 85 Tamura H, Yamazaki H, Sato H, Sakaki S. J. Am. Chem. Soc. 2003; 125: 16114
  • 86 Sumimoto M, Iwane N, Takahama T, Sakaki S. J. Am. Chem. Soc. 2004; 126: 10457
  • 87 Lam WH, Lam KC, Lin Z, Shimada S, Perutz RN, Marder TB. Dalton Trans. 2004; 1556
  • 88 Vanchura II BA, Preshlock SM, Roosen PC, Kallepalli VA, Staples RJ, Maleczka Jr RE, Singleton DA, Smith III MR. Chem. Commun. (Cambridge) 2010; 46: 7724
  • 89 Roosen PC, Kallepalli VA, Chattopadhyay B, Singleton DA, Maleczka Jr RE, Smith III MR. J. Am. Chem. Soc. 2012; 134: 11350
  • 90 Jover J, Maseras F. Organometallics 2016; 35: 3221
  • 91 Li H, Obligacion JV, Chirik PJ, Hall MB. ACS Catal. 2018; 8: 10606
  • 92 Bai H, Xu H, Zhang H, Guo Y, Shan J, Wei D, Zhu Y, Zhang S, Zhang W. Catal. Sci. Technol. 2018; 8: 5165
  • 93 Zou X, Zhao H, Li Y, Gao Q, Ke Z, Xu S. J. Am. Chem. Soc. 2019; 141: 5334
  • 94 Reyes RL, Iwai T, Maeda S, Sawamura M. J. Am. Chem. Soc. 2019; 141: 6817
  • 95 Webster CE, Fan Y, Hall MB, Kunz D, Hartwig JF. J. Am. Chem. Soc. 2003; 125: 858
  • 96 Hartwig JF, Cook KS, Hapke M, Incarvito CD, Fan Y, Webster CE, Hall MB. J. Am. Chem. Soc. 2005; 127: 2538
  • 97 Wei CS, Jiménez-Hoyos CA, Videa MF, Hartwig JF, Hall MB. J. Am. Chem. Soc. 2010; 132: 3078
  • 98 Huang G, Kalek M, Liao R.-Z, Himo F. Chem. Sci. 2015; 6: 1735
  • 99 Haines BE, Saito Y, Segawa Y, Itami K, Musaev DG. ACS Catal. 2016; 6: 7536
  • 100 Kelly CM, Fuller III JT, Macaulay CM, McDonald R, Ferguson MJ, Bischof SM, Sydora OL, Ess DH, Stradiotto M, Turculet L. Angew. Chem. Int. Ed. 2017; 56: 6312
  • 101 Lam KC, Marder TB, Lin Z. Organometallics 2010; 29: 1849
  • 102 Cheung MS, Sheong FK, Marder TB, Lin Z. Chem.–Eur. J. 2015; 21: 7480
  • 103 Li Q, Liskey CW, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 8755