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

Barday, Manuel and Janot, Christopher and Halcovitch, Nathan R. and Muir, James and Aissa, Christophe (2017) Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds. Angewandte Chemie International Edition, 56 (42). pp. 13117-13121. ISSN 1433-7851

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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.

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Journal Article
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Angewandte Chemie International Edition
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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 This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
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11 Sep 2017 12:20
Last Modified:
28 May 2023 03:49