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Concise Synthesis of Polysubstituted Carbohelicenes by a C−H Activation/Radical Reaction/C−H Activation Sequence
Author(s) -
Yin Jiangliang,
You Jingsong
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811023
Subject(s) - chemoselectivity , chemistry , regioselectivity , radical , cascade reaction , electron paramagnetic resonance , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , physics , nuclear magnetic resonance
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.