10 Borylation Reactions in Water
Book
Editor: Fernández, E.
Title: Advances in Organoboron Chemistry towards Organic Synthesis
Print ISBN: 9783132429710; Online ISBN: 9783132429758; Book DOI: 10.1055/b-006-164898
2020 © 2020. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
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 (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
Abstract
Organoboron compounds are integral to modern synthetic organic chemistry as their C–B linkages undergo a range of chemical transformations. Their privileged position is underpinned by their versatile transformability with retention of stereochemistry, as well as their non-toxic nature and excellent functional-group tolerance. Although water has become a common medium in the reaction of organoboron compounds, such as Suzuki–Miyaura couplings, C–B bond formations in aqueous media have emerged only recently. This chapter offers an overview of recent developments across the broad landscape of organoboron chemistry, using solvent amounts of water and covering a range of C–B bond-formation processes, including enantioselective reactions.
Key words
water - aqueous - bis(pinacolato)diboron - tetrahydroxydiboron - Miyaura borylation - photolysis - photoredox - visible light - arenediazonium salts - diazo compounds - arylboronates - vinylboronates - allylboronates - alkylboronates - boranes - reductive borylation - hydroboration - ring opening - decarboxylation - photopolymerization - conjugate addition - 1,6-addition - asymmetric synthesis - palladium - copper - photocatalysis - N-heterocyclic carbenes (NHC) - porphyrins - directed evolution - cytochrome - surfactants - heterogeneous catalysis - continuous flow- 1 Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. D. G. Hall,. Wiley-VCH; Weinheim, Germany 2011
- 2 Synthesis and Application of Organoboron Compounds. E. Fernández,, A. Whiting,. Springer; Cham, Switzerland 2015
- 4 E. C. Neeve,, S. J. Geier,, I. A. I. Mkhalid,, S. A. Westcott,, T. B. Marder,. Chem. Rev.. 2016; 116: 9091
- 10 A. Zernickel,, W. Du,, S. A. Ghorpade,, D. N. Sawant,, A. A. Makki,, N. Sekar,, J. Eppinger,. J. Org. Chem.. 2018; 83: 1842
- 17 C.-T. Yang,, Z.-Q. Zhang,, H. Tajuddin,, C.-C. Wu,, J. Liang,, J.-H. Liu,, Y. Fu,, M. Czyzewska,, P. G. Steel,, T. B. Marder,, L. Liu,. Angew. Chem. Int. Ed.. 2012; 51: 528
- 18 A. Joshi-Pangu,, X. Ma,, M. Diane,, S. Iqbal,, R. J. Kribs,, R. Huang,, C.-Y. Wang,, M. R. Biscoe,. J. Org. Chem.. 2012; 77: 6629
- 22 C.-C. Tai,, M.-S. Yu,, Y.-L. Chen,, W.-H. Chuang,, T.-H. Lin,, G. P. A. Yap,, T.-G. Ong,. Chem. Commun. (Cambridge). 2014; 50: 4344
- 34 M. Isegawa,, W. M. C. Sameera,, A. K. Sharma,, T. Kitanosono,, M. Kato,, S. Kobayashi,, K. Morokuma,. ACS Catal.. 2017; 7: 5370
- 35 M.-A. Tehfe,, J. Monot,, M. Malacria,, L. Fensterbank,, J.-P. Fouassier,, D. P. Curran,, E. Lacôte,, J. Lalevée,. ACS Macro Lett.. 2012; 1: 92
- 37 X. Huang,, M. Garcia-Borràs,, K. Miao,, S. B. J. Kan,, A. Zutshi,, K. N. Houk,, F. H. Arnold,. ACS Cent. Sci.. 2019; 5: 270
- 38 K. Chen,, X. Huang,, S.-Q. Zhang,, A. Z. Zhou,, S. B. J. Kan,, X. Hong,, F. H. Arnold,. Synlett. 2019; 30: 378
- 39 D. Hemming,, R. Fritzemeier,, S. A. Westcott,, W. L. Santos,, P. G. Steel,. Chem. Soc. Rev.. 2018; 47: 7477
- 44 S. Kobayashi,, P. Xu,, T. Endo,, M. Ueno,, T. Kitanosono,. Angew. Chem. Int. Ed.. 2012; 51: 12763
- 48 T. Kitanosono,, P. Xu,, S. Isshiki,, L. Zhu,, S. Kobayashi,. Chem. Commun. (Cambridge). 2014; 50: 9336
- 49 R. Gandolfi,, G. Facchetti,, M. S. Christodoulou,, M. Fuse,, F. Meneghetti,, I. Rimoldi,. ChemistryOpen. 2018; 7: 393
- 51 S. W. Reilly,, G. Akurathi,, H. K. Box,, H. U. Valle,, T. K. Hollis,, C. E. Webster,. J. Organomet. Chem.. 2016; 802: 32