C(sp³)-C(sp²) cross-coupling of alkylsilicates with borylated aryl bromides - an iterative platform to alkylated aryl- and heteroaryl boronates.

ABSTRACT: The attractive field of iterative cross-coupling has seen numerous advances, although almost exclusively in the union of sp²-hybridized partners. Conspicuously absent from this useful synthetic manifold is the inclusion of sp³-hybridized pronucleophiles that can undergo transmetalation under mild conditions. Described here is the use of primary and secondary ammonium alkylsilicates, which undergo facile C(sp³)-C(sp²) cross-coupling with borylated aryl bromide partners under photoredox/nickel dual catalysis conditions. This operationally simple procedure allows the production of alkylated small molecules possessing boronate ester (BPin, Bneopentyl, BMIDA) functional handles. Because of the extremely mild reaction conditions and the innocuous bypro

SUBMITTER: Vara BA 

PROVIDER: S-EPMC5351799 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature