Organic Letters p. 5300 - 5303 (2018)
Update date:2022-08-02
Topics:
Corless, Victoria B.
Holownia, Aleksandra
Foy, Hayden
Mendoza-Sanchez, Rodrigo
Adachi, Shinya
Dudding, Travis
Yudin, Andrei K.
As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.
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