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Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds

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<mark>Journal publication date</mark>9/10/2017
<mark>Journal</mark>Angewandte Chemie International Edition
Issue number42
Number of pages5
Pages (from-to)13117-13121
Early online date29/08/17
<mark>Original language</mark>English


The functionalization of carbon-hydrogen bonds in non-nucleophilic substrates using α-carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that those reagents would provide over diazo compounds or their in situ precursors. We describe the cross-coupling reactions of sulfoxonium ylides with C(sp2)-H bond of arenes and heteroarenes in the presence of a rhodium catalyst. The reaction proceeds by a succession of C-H activation, migratory insertion of the ylide into the carbon-metal bond and protonation, the last step being turnover-limiting. The method is applied to the synthesis of benz[c]acridines when allied to an iridium-catalyzed dehydrative cyclization.

Bibliographic note

This is the peer reviewed version of the following article: M. Barday, C. Janot, N. R. Halcovitch, J. Muir, C. Aïssa, Angew. Chem. Int. Ed. 2017, 56, 13117. doi:10.1002/anie.201706804 which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201706804/abstract This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.