CuBr-Mediated One-Pot Synthesis of Sulfonyl 9-Fluorenylidenes.

J Org Chem

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.

Published: June 2020

In this article, a high-yield method for the synthesis of sulfonyl 9-fluorenylidenes is described, which consists of a one-pot straightforward three-step synthetic route, including (i) CuBr-mediated α-bromination of -arylacetophenone, (ii) sequential nucleophilic substitution of the resulting α-bromo -arylacetophenone with sodium sulfinate (RSONa), and (iii) the CuBr-mediated intramolecular Friedel-Crafts cyclizative dehydration. A plausible mechanism is proposed and discussed. This protocol provides a highly effective regio- and stereoselective annulation via the formation of one carbon-carbon (C-C) bond and one carbon-sulfur (C-S) bond.

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http://dx.doi.org/10.1021/acs.joc.0c00035DOI Listing

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