Gallou, Fabrice (2023) Surfactant + water: efficient solution to trigger undirected & mild C–H activation of (oligo)thiophenes at challenging β-position. Angewandte Chemie. International edition, 14. pp. 12049-12055.

Abstract

Unexpected potential of micellar medium to achieve challenging β-selective direct arylation of (oligo)thiophenes is reported. Thanks to the use of water/surfactant solution in combination with natural feedstock derived undecanoic acid additive, this high-yielding C–H coupling could be performed regioselective at room temperature. Broad functional group tolerance was shown with respect to the coupling partners and the synthetic value of this catalytic system has been exemplified by the late-stage diversification of Ticlopidine. Remarkably, this protocol is also compatible with oligothiophenes, allowing fully selective functionalization of such molecules of interest exclusively at their external positions, thus allowing late-stage diversification of important motifs for organic materials.

Item Type:	Article
Date Deposited:	02 Jul 2024 00:46
Last Modified:	02 Jul 2024 00:46
URI:	https://oak.novartis.com/id/eprint/50089