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.

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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:	19 Jan 2023 00:21
DOI:	10.1002/anie.201910821
Open Access URL:	https://doi.org/10.1002/anie.201910821
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3059894

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• Chemospecific Cyclizations of alpha-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls. (deposited 30 Sep 2019 09:18)
  • Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls. (deposited 30 Oct 2019 08:25) [Currently Displayed]