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Fernández, E.: 2020 Science of Synthesis, 2019/6: Advances in Organoboron Chemistry towards Organic Synthesis DOI: 10.1055/sos-SD-230-00161
Advances in Organoboron Chemistry towards Organic Synthesis

9 Decarbonylative/Decarboxylative Borylation

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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

2020 © 2020 Georg Thieme Verlag KG
Georg Thieme Verlag KG, Stuttgart

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

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

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

Type: Multivolume Edition

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Abstract

Organoboron species are versatile building blocks and have been widely used in the synthesis of bioactive molecules, natural products, and organic materials. Accordingly, approaches to access such compounds have been widely explored. Carboxylic acids, which are ubiquitous and abundant organic feedstocks, can be transformed into their borylated counterparts via several different catalytic or stoichiometric approaches. In this review, decarboxylative borylation reactions, which form a carbon–boron bond with elimination of carbon dioxide, are detailed in terms of reaction conditions, substrate scope, and experimental procedures.

Key words

decarboxylative borylation - decarbonylative borylation - decarboxylation - borylation - carboxylic acids - boronic acids - boronic acid esters - boronates - light-induced reaction - photoredox catalysis - nickel catalysis - copper catalysis - redox-activated esters - N-hydroxyphthalimides
 
  • 1 J. W. B. Fyfe,, A. J. B. Watson,. Chem. 2017; 3: 31
    Google Scholar
  • 2 E. C. Neeve,, S. J. Geier,, I. A. I. Mkhalid,, S. A. Westcott,, T. B. Marder,. Chem. Rev.. 2016; 116: 9091
    Google Scholar
  • 3 V. D. Nguyen,, V. T. Nguyen,, S. Jin,, H. T. Dang,, O. V. Larionov,. Tetrahedron. 2019; 75: 584
    Google Scholar
  • 4 G. Yan,, D. Huang,, X. Wu,. Adv. Synth. Catal.. 2018; 360: 1040
    Google Scholar
  • 5 L. Xu,, G. Wang,, S. Zhang,, H. Wang,, L. Wang,, L. Liu,, J. Jiao,, P. Li,. Tetrahedron. 2017; 73: 7123
    Google Scholar
  • 6 Y. Wei,, P. Hu,, M. Zhang,, W. Su,. Chem. Rev.. 2017; 117: 8864
    Google Scholar
  • 7 T. Patra,, D. Maiti,. Chem.–Eur. J.. 2017; 23: 7382
    Google Scholar
  • 8 J. Schwarz,, B. König,. Green Chem.. 2018; 20: 323
    Google Scholar
  • 9 P. Bharathi,, H. Zhao,, S. Thayumanavan,. Org. Lett.. 2001; 3: 1961
    Google Scholar
  • 10 K. P. Melnykov,, D. S. Granat,, D. M. Volochnyuk,, S. V. Ryabukhin,, O. O. Grygorenko,. Synthesis. 2018; 50: 4949
    Google Scholar
  • 11 L. Guo,, M. Rueping,. Acc. Chem. Res.. 2018; 51: 1185
    Google Scholar
  • 12 L. Guo,, M. Rueping,. Chem.–Eur. J.. 2016; 22: 16787
    Google Scholar
  • 13 X. Pu,, J. Hu,, Y. Zhao,, Z. Shi,. ACS Catal.. 2016; 6: 6692
    Google Scholar
  • 14 J. Hu,, Y. Zhao,, J. Liu,, Y. Zhang,, Z. Shi,. Angew. Chem. Int. Ed.. 2016; 55: 8718
    Google Scholar
  • 15 S.-C. Lee,, L. Guo,, H. Yue,, H.-H. Liao,, M. Rueping,. Synlett. 2017; 28: 2594
    Google Scholar
  • 16 H. Ochiai,, Y. Uetake,, T. Niwa,, T. Hosoya,. Angew. Chem. Int. Ed.. 2017; 56: 2482
    Google Scholar
  • 17 T. Niwa,, H. Ochiai,, M. Isoda,, T. Hosoya,. Chem. Lett.. 2017; 46: 1315
    Google Scholar
  • 18 C. A. Malapit,, N. Ichiishi,, M. S. Sanford,. Org. Lett.. 2017; 19: 4142
    Google Scholar
  • 19 Z. Wang,, X. Wang,, Y. Nishihara,. Chem. Commun. (Cambridge). 2018; 54: 13969
    Google Scholar
  • 20 C. Liu,, C.-L. Ji,, X. Hong,, M. Szostak,. Angew. Chem. Int. Ed.. 2018; 57: 16721
    Google Scholar
  • 22 K. Okada,, K. Okamoto,, M. Oda,. J. Am. Chem. Soc.. 1988; 110: 8736
    Google Scholar
  • 23 C. Li,, J. Wang,, L. M. Barton,, S. Yu,, M. Tian,, D. S. Peters,, M. Kumar,, A. W. Yu,, K. A. Johnson,, A. K. Chatterjee,, M. Yan,, P. S. Baran,. Science (Washington, D. C.). 2017; 356: 1045
    Google Scholar
  • 24 J. Wang,, M. Shang,, H. Lundberg,, K. S. Feu,, S. J. Hecker,, T. Qin,, D. G. Blackmond,, P. S. Baran,. ACS Catal.. 2018; 8: 9537
    Google Scholar
  • 25 D. Hu,, L. Wang,, P. Li,. Org. Lett.. 2017; 19: 2770
    Google Scholar
  • 26 A. Fawcett,, J. Pradeilles,, Y. Wang,, T. Mutsuga,, E. L. Myers,, V. K. Aggarwal,. Science (Washington, D. C.). 2017; 357: 283
    Google Scholar
  • 27 L. Candish,, M. Teders,, F. Glorius,. J. Am. Chem. Soc.. 2017; 139: 7440
    Google Scholar
  • 28 W.-M. Cheng,, R. Shang,, B. Zhao,, W.-L. Xing,, Y. Fu,. Org. Lett.. 2017; 19: 4291
    Google Scholar
  • 29 Q. Feng,, K. Yang,, Q. Song,. Chem. Commun. (Cambridge). 2015; 51: 15394
    Google Scholar
  • 30 F. M. Irudayanathan,, G. C. E. Raja,, H.-S. Kim,, K. Na,, S. Lee,. Bull. Korean Chem. Soc.. 2016; 37: 463
    Google Scholar
  • 31 Y.-W. Zhao,, Q. Feng,, Q.-L. Song,. Chin. Chem. Lett.. 2016; 27: 571
    Google Scholar