Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes?

Chemical Science Pub Date: 2019-11-11 DOI: 10.1039/C9SC04308J

Abstract

Rhodium(II)-catalyzed unusual branch-selective ortho-C–H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the para-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C–H alkylated byproducts. The results of deuterium labeling experiments suggest that both hydrometalation and carbometalation pathways are involved in this conversion.

Graphical abstract: Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
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