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Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
Author(s) -
Clare Daniel,
Dobson Benjamin C.,
Inglesby Phillip A.,
Aïssa Christophe
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201910821
Subject(s) - aryl , surface modification , chemistry , iridium , catalysis , organic chemistry , alkyl
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.