One-Pot Synthesis of Dihydrobenzo[]fluorenes via Cascade C-H Annulation of Thiobenzamide with Alkynes.

J Org Chem

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China.

Published: September 2024

We herein disclose a highly efficient one-pot synthetic strategy for dihydrobenzo[]fluorenes via cascade rhodium(III)-catalyzed -C-H activation/annulation of thiobenzamides with aryl ethynyl ketones and subsequently copper(II)-promoted intramolecular C-H/C-H cross-coupling reactions. Mechanistic investigations suggest that Cu(II) plays two crucial roles by serving as a sulfide scavenger to regenerate the Rh(III) catalyst and promoting the intramolecular C-H/C-H cross-coupling reaction. This protocol greatly streamlines accesses to a variety of appealing tetracyclic benzo[]fluorene skeletons, which may have potential biological activity and medicinal properties.

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http://dx.doi.org/10.1021/acs.joc.4c01228DOI Listing

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