Rh-Catalyzed C-H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration.

Rh-Catalyzed C-H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration.
Chem Commun (Camb). 2018 May 17;:
Authors: Zhou L, Zhu C, Loh TP, Feng C
Abstract
Herein we demonstrate that an alkylation of indoles could be accessed through C-H bond functionalization with α,α-difluorovinyl tosylate. The key aspect for the effective alkylation is the influence of the fluorine substituents on the reactivity of the C[double bond, length as m-dash]C double bond, allowing regioselective insertion as well as an indolyl group shift process. Furthermore, the fluorides are removed through alcoholysis to furnish the alkylation product as a traceless auxiliary.
PMID: 29770372 [PubMed - as supplied by publisher]

Source: Chemical Communications - May 17, 2018 Category: Chemistry Authors: Zhou L, Zhu C, Loh TP, Feng C Tags: Chem Commun (Camb) Source Type: research