Concise Synthesis of Polysubstituted Carbohelicenes by a C-H Activation/Radical Reaction/C-H Activation Sequence.

Angew Chem Int Ed Engl

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

Published: January 2019

Disclosed herein is the merging of C-H activation and radical chemistry, enabling rapid access to a structurally diverse family of fused carbohelicenes through the fusion of α-acetylnaphthalenes with alkynes under oxidative conditions. This cascade process exhibits exquisite chemoselectivity and regioselectivity. The reaction pathway was analyzed by intermediate separations, control experiments, radical trapping, EPR, MALDI-TOF-MS, and ESI-HRMS experiments, and shown to involve a C2-H activation/radical reaction/C8-H activation relay.

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http://dx.doi.org/10.1002/anie.201811023DOI Listing

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