Exploration of mild copper-mediated coupling of organotrifluoroborates in syntheses of thiirane-based inhibitors of matrix metalloproteinases

SEBASTIAN A. TESTERO; RENEE BOULEY; JED F. FISHER; MAYLAND CHANG; SHAHRIAR MOBASHERY

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2011 vol. 21 p. 1565 - 1567

0960-894X

The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.