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Updated: Jan 19, 2026
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
Daniel Clare1, Benjamin C Dobson2, Phillip A Inglesby2
1Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
Abstract:
The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.
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