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Tetrahedron. 2018 Jun 28;74(26):3318-3324. doi: 10.1016/j.tet.2018.03.062. Epub 2018 Mar 31.

Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles.

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1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

Abstract

The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles with different substitution patterns as well as C-alkenyl triazoles were effective inputs. The reaction could also be performed under straightforward bench top conditions.

KEYWORDS:

Catalysis; C–H functionalization; Nitrogen heterocycle; Rhodium; Sulfoxonium ylide

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