Fensterbank, L.  et al.: 2021 Science of Synthesis, 2020/4: Free Radicals: Fundamentals and Applications in Organic Synthesis 1 DOI: 10.1055/sos-SD-234-00203
Free Radicals: Fundamentals and Applications in Organic Synthesis 1

1.10 Boron-Centered Radicals

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Book

Editors: Fensterbank, L. ; Ollivier, C.

Authors: André-Joyaux, E.; Bellanger, C.; Bertrand, M. P.; Besson, E. ; Bietti, M.; Braïda, B.; Cahoon, S. B.; Casano, G.; Chelli, S.; Chen, Y.; Chiba, S. ; Dénès, F. ; Derat, E.; Gastaldi, S. ; Gnägi, L.; Kaga, A.; Lakhdar, S. ; Liu, D.; Lu, X.-L.; Maestri, G. ; Melendez, C.; Ouari, O. ; Renaud, P. ; Rovis, T.; Serafino, A.; Shirakawa, E. ; Soulard, V.; Treacy, S. M.; Wang, B.; Wang, Y.-F.; Yoon, T. P.; Yorimitsu, H.; Zhang, F.-L.; Zhang, J.; Zhang, X.

Title: Free Radicals: Fundamentals and Applications in Organic Synthesis 1

Print ISBN: 9783132435520; Online ISBN: 9783132435537; Book DOI: 10.1055/b000000087

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.; Fürstner, A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L

Type: Multivolume Edition

 


Abstract

Boryl radicals have emerged as powerful radical intermediates in organic synthesis. This review summarizes recently developed transformations involving boryl radical species, including C—B bond formation reactions, reduction reactions, and radical catalysis.

 
  • 1 Baban JA, Roberts BP. J. Chem. Soc., Chem. Commun. 1983; 1224
  • 2 Rablen PR. J. Am. Chem. Soc. 1997; 119: 8350
  • 3 Roberts BP. Chem. Soc. Rev. 1999; 28: 25
  • 4 Ueng S.-H, Brahmi MM, Derat É, Fensterbank L, Lacôte E, Malacria M, Curran DP. J. Am. Chem. Soc. 2008; 130: 10082
  • 5 Ueng S.-H, Solovyev A, Yuan X, Geib SJ, Fensterbank L, Lacôte E, Malacria M, Newcomb M, Walton JC, Curran DP. J. Am. Chem. Soc. 2009; 131: 11256
  • 6 Walton JC, Brahmi MM, Fensterbank L, Lacôte E, Malacria M, Chu Q, Ueng S.-H, Solovyev A, Curran DP. J. Am. Chem. Soc. 2010; 132: 2350
  • 7 Taniguchi T. Eur. J. Org. Chem. 2019; 6308
  • 8 Mo F, Jiang Y, Qiu D, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 1846
  • 9 Friese FW, Studer A. Chem. Sci. 2019; 10: 8503
  • 10 Yan G, Huang D, Wu X. Adv. Synth. Catal. 2018; 360: 1040
  • 11 Zhang F.-L, Wang Y.-F. Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis. 2019. 1. 355
  • 12 Ren S.-C, Zhang F.-L, Xu A.-Q, Yang Y, Zheng M, Zhou X, Fu Y, Wang Y.-F. Nat. Commun. 2019; 10: 1934
  • 13 Huang Y.-S, Wang J, Zheng W.-X, Zhang F.-L, Yu Y.-J, Zheng M, Zhou X, Wang Y.-F. Chem. Commun. (Cambridge) 2019; 55: 11904
  • 14 Jin J.-K, Zheng W.-X, Xia H.-M, Zhang F.-L, Wang Y.-F. Org. Lett. 2019; 21: 8414
  • 15 Liu X, Lin EE, Chen G, Li J.-L, Liu P, Wang H. Org. Lett. 2019; 21: 8454
  • 16 Dai W, Geib SJ, Curran DP. J. Am. Chem. Soc. 2019; 141: 12355
  • 17 Watanabe T, Hirose D, Curran DP, Taniguchi T. Chem.–Eur. J. 2017; 23: 5404
  • 18 Shimoi M, Kevlishvili I, Watanabe T, Maeda K, Geib SJ, Curran DP, Liu P, Taniguchi T. Angew. Chem. Int. Ed. 2020; 59: 903
  • 19 Takahashi K, Shimoi M, Watanabe T, Maeda K, Geib SJ, Curran DP, Taniguchi T. Org. Lett. 2020; 22: 2054
  • 20 Zhou N, Yuan X.-A, Zhao Y, Xie J, Zhu C. Angew. Chem. Int. Ed. 2018; 57: 3990
  • 21 Xia P.-J, Song D, Ye Z.-P, Hu Y.-Z, Xiao J.-A, Xiang H.-Y, Chen X.-Q, Yang H. Angew. Chem. Int. Ed. 2020; 59: 6706
  • 22 Xia P.-J, Ye Z.-P, Hu Y.-Z, Xiao J.-A, Chen K, Xiang H.-Y, Chen X.-Q, Yang H. Org. Lett. 2020; 22: 1742
  • 23 Dai W, Geib SJ, Curran DP. J. Am. Chem. Soc. 2020; 142: 6261
  • 24 Qi J, Zhang F.-L, Jin J.-K, Zhao Q, Li B, Liu L.-X, Wang Y.-F. Angew. Chem. Int. Ed. 2020; 59: 12876
  • 25 Kawamoto T, Okada T, Curran DP, Ryu I. Org. Lett. 2013; 15: 2144
  • 26 Jin J.-K, Zhang F.-L, Wang Y.-F. Huaxue Xuebao 2019; 77: 889
  • 27 Xu A.-Q, Zhang F.-L, Ye T, Yu Z.-X, Wang Y.-F. CCS Chem. 2019; 1: 504
  • 28 Chen K, Zhang S, He P, Li P. Chem. Sci. 2016; 7: 3676
  • 29 Qiao Y, Yang Q, Schelter EJ. Angew. Chem. Int. Ed. 2018; 57: 10999
  • 30 Liu Q, Hong J, Sun B, Bai G, Li F, Liu G, Yang Y, Mo F. Org. Lett. 2019; 21: 6597
  • 31 Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440
  • 32 Cheng W.-M, Shang R, Zhao B, Xing W.-L, Fu Y. Org. Lett. 2017; 19: 4291
  • 33 Hu D, Wang L, Li P. Org. Lett. 2017; 19: 2770
  • 34 Fawcett A, Pradeilles J, Wang Y, Mutsuga T, Myers EL, Aggarwal VK. Science (Washington, D. C.) 2017; 357: 283
  • 35 Wang J, Shang M, Lundberg H, Feu KS, Hecker SJ, Qin T, Blackmond DG, Baran PS. ACS Catal. 2018; 8: 9537
  • 36 Wu J, He L, Noble A, Aggarwal VK. J. Am. Chem. Soc. 2018; 140: 10700
  • 37 Sandfort F, Strieth-Kalthoff F, Klauck FJR, James MJ, Glorius F. Chem.–Eur. J. 2018; 24: 17210
  • 38 Kubota K, Pang Y, Miura A, Ito H. Science (Washington, D. C.) 2019; 366: 1500
  • 39 Liu W, Yang X, Gao Y, Li C.-J. J. Am. Chem. Soc. 2017; 139: 8621
  • 40 Lu X, Zhang Z.-Q, Yu L, Zhang B, Wang B, Gong T.-J, Tian C.-L, Xiao B, Fu Y. Chin. J. Chem. 2019; 37: 11
  • 41 Friese FW, Studer A. Angew. Chem. Int. Ed. 2019; 58: 9561
  • 42 Wu J, Bär RM, Guo L, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2019; 58: 18830
  • 43 Mazzarella D, Magagnano G, Schweitzer-Chaput B, Melchiorre P. ACS Catal. 2019; 9: 5876
  • 44 Huang C, Feng J, Ma R, Fang S, Lu T, Tang W, Du D, Gao J. Org. Lett. 2019; 21: 9688
  • 45 Zhang J.-J, Duan X.-H, Wu Y, Yang J.-C, Guo L.-N. Chem. Sci. 2019; 10: 161
  • 46 Wang G, Cao J, Gao L, Chen W, Huang W, Cheng X, Li S. J. Am. Chem. Soc. 2017; 139: 3904
  • 47 Cao J, Wang G, Gao L, Cheng X, Li S. Chem. Sci. 2018; 9: 3664
  • 48 Gao L, Wang G, Cao J, Yuan D, Xu C, Guo X, Li S. Chem. Commun. (Cambridge) 2018; 54: 11534
  • 49 Cheng Y, Mück-Lichtenfeld C, Studer A. J. Am. Chem. Soc. 2018; 140: 6221
  • 50 Cao J, Wang G, Gao L, Chen H, Liu X, Cheng X, Li S. Chem. Sci. 2019; 10: 2767
  • 51 Koniarczyk JL, Greenwood JW, Alegre-Requena JV, Paton RS, McNally A. Angew. Chem. Int. Ed. 2019; 58: 14882
  • 52 Guo A, Han J.-B, Tang X.-Y. Org. Lett. 2018; 20: 2351
  • 53 Guo A, Han J.-B, Zhu L, Wei Y, Tang X.-Y. Org. Lett. 2019; 21: 2927
  • 54 Zhao D, Xie Z. Angew. Chem. Int. Ed. 2016; 55: 3166
  • 55 Mills HA, Martin JL, Rheingold AL, Spokoyny AM. J. Am. Chem. Soc. 2020; 142: 4586