ReO/HReO Mediated Intramolecular Hydroacyloxylation of Unactivated Alkenes: A Dual Hydrogen-Bonding Effect.

Org Lett

Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Materials Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.

Published: January 2023

This publication describes the application of ReO in hexafluoroisopropanol (HFIP) for the activation of inert as well as electronically deactivated olefins to facilitate a challenging intramolecular hydroacyloxylation reaction. Both HFIP and an internal carboxy group have been proven to be crucial for the successful implementation of this transformation; these are proposed to assist the formation and stabilization of the key cationic intermediate via hydrogen-bonding interactions with perrhenate anion (ReO).

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http://dx.doi.org/10.1021/acs.orglett.2c03846DOI Listing

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