Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

Victoria B Corless; Aleksandra Holownia; Hayden Foy; Rodrigo Mendoza-Sanchez; Shinya Adachi; Travis Dudding; Andrei K Yudin

doi:10.1021/acs.orglett.8b02234

Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

Org Lett. 2018 Sep 7;20(17):5300-5303. doi: 10.1021/acs.orglett.8b02234. Epub 2018 Aug 21.

Authors

Victoria B Corless¹, Aleksandra Holownia¹, Hayden Foy², Rodrigo Mendoza-Sanchez¹, Shinya Adachi¹, Travis Dudding², Andrei K Yudin¹

Affiliations

¹ Davenport Research Laboratories, Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , ON M5S 3H6 , Canada.
² Department of Chemistry , Brock University , 1812 Sir Isaac Brock Way , St. Catherines , ON L2S 3A1 , Canada.

PMID: 30129366
DOI: 10.1021/acs.orglett.8b02234

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't