Iridium-Catalyzed, Hydrosilyl-Directed Borylation of Unactivated Alkyl C-H Bonds.

ABSTRACT: We report the iridium-catalyzed borylation of primary and secondary alkyl C-H bonds directed by a Si-H group to form alkylboronate esters site selectively. The reactions occur with high selectivity at primary C-H bonds ? to the hydrosilyl group to form primary alkyl bisboronate esters. In the absence of such primary C-H bonds, the borylation occurs selectively at a secondary C-H bond ? to the hydrosilyl group, and these reactions of secondary C-H bonds occur with high diastereoselectivity. The hydrosilyl-containing alkyl boronate esters formed by this method undergo transformations selectively at the carbon-boron or carbon-silicon bonds of these products under distinct conditions to give the products of amination, oxidation, and arylation.

SUBMITTER: Larsen MA 

PROVIDER: S-EPMC4809204 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature