Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls


Clare, Daniel, Dobson, Benjamin C, Inglesby, Phillip A and Aissa, C ORCID: 0000-0003-0750-9435 (2019) Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls Angewandte Chemie (International Edition), 58 (45). pp. 16198-16202. ISSN 1433-7851, 1521-3773

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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.

Item Type: Article
Uncontrolled Keywords: chemospecificity, cyclization, hexafluoroisopropanol, iridium, sulfoxonium
Depositing User: Symplectic Admin
Date Deposited: 30 Oct 2019 08:25
Last Modified: 01 Mar 2026 08:42
DOI: 10.1002/anie.201910821
Open Access URL: https://doi.org/10.1002/anie.201910821
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URI: https://livrepository.liverpool.ac.uk/id/eprint/3059894
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