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Chemospecific Cyclizations of ?-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls.

ABSTRACT: The functionalization of aryl and heteroaryls using ?-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 ?-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.

SUBMITTER: Clare D 

PROVIDER: S-EPMC6856693 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Clare Daniel D   Dobson Benjamin C BC   Inglesby Phillip A PA   Aïssa Christophe C  

Angewandte Chemie (International ed. in English) 20190924 45

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, t  ...[more]

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