Rights statement: 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.
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Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds
AU - Barday, Manuel
AU - Janot, Christopher
AU - Halcovitch, Nathan R.
AU - Muir, James
AU - Aissa, Christophe
N1 - 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.
PY - 2017/10/9
Y1 - 2017/10/9
N2 - 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.
AB - 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.
KW - Sulfoxonium
U2 - 10.1002/anie.201706804
DO - 10.1002/anie.201706804
M3 - Journal article
C2 - 28853234
VL - 56
SP - 13117
EP - 13121
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
IS - 42
ER -