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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.