Categories: C-B Bond Formation > Synthesis of boronic acids and boronates >
Synthesis of α-haloboronates
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A highly efficient deoxygenative haloboration of aldehydes provides secondary
α-haloboronates. Even tertiary α-haloboronates can be readily prepared via the
same strategy with ketones. Furthermore, enantioselective chloroboration of
carbonyls was successfully achieved to give chiral secondary or tertiary
α-chloroboronates.
D. Wang, J. Zhou, Z. Hu, T. Xu, J. Am. Chem. Soc.,
2022, 144, 22870-22876.
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α-Halogenated boronic esters are versatile building blocks. A convenient
visible light-induced C-H bromination reaction of readily available benzyl
boronic esters provides α-brominated boronates in high yields under mild
conditions and with good functional group tolerance. The analogous chlorides and
iodides can be accessed via Finkelstein reaction.
F.-C. Gao, M. Li, H.-Y. Gu, X.-Y. Chen, S. Xu, Y. Wei, K. Hong, J. Org. Chem., 2023, 88,
14246-14254.
A Cu-catalyzed atom transfer radical addition (ATRA) of alkyl halides to
vinyl boronic esters provides α-haloboronic esters. The catalyst is proposed to
mediate a traditionally inefficient halogen atom transfer of the α-boryl radical
intermediate. Further, a one-pot, two-step protocol enables direct access to an
array of α-functionalized products.
T. D. Ho, B. J. Lee, C. Tan, J. A. Utley, N. Q. Ngo, K. L. Hull, J. Am. Chem. Soc.,
2023, 145, 27230-27235.