A Rh(II)-catalyzed formal 1,3-dichalcogenation of vinyl carbenes is described using stable hydrazones as carbene precursors and disulfides and diselenides as chalcogen sources. The reaction proceeds with excellent regio- and stereoselectivities under mild conditions, with the 1,4-sigmatropic migration of an ylidic intermediate being a key step. Mechanistic studies support a concerted pathway of chalcogen migration.
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J. Wang
Bin Wei
Xiang Gao
Organic Letters
Shandong University
Shaanxi Normal University
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Wang et al. (Mon,) studied this question.
www.synapsesocial.com/papers/69df2b04e4eeef8a2a6b00b9 — DOI: https://doi.org/10.1021/acs.orglett.6c00809