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  • Barday_et_al-2017-Angewandte_Chemie_International_Edition

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

Research output: Contribution to Journal/MagazineJournal articlepeer-review

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Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds. / Barday, Manuel; Janot, Christopher; Halcovitch, Nathan R. et al.
In: Angewandte Chemie International Edition, Vol. 56, No. 42, 09.10.2017, p. 13117-13121.

Research output: Contribution to Journal/MagazineJournal articlepeer-review

Harvard

Barday, M, Janot, C, Halcovitch, NR, Muir, J & Aissa, C 2017, 'Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds', Angewandte Chemie International Edition, vol. 56, no. 42, pp. 13117-13121. https://doi.org/10.1002/anie.201706804

APA

Barday, M., Janot, C., Halcovitch, N. R., Muir, J., & Aissa, C. (2017). Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds. Angewandte Chemie International Edition, 56(42), 13117-13121. https://doi.org/10.1002/anie.201706804

Vancouver

Barday M, Janot C, Halcovitch NR, Muir J, Aissa C. Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds. Angewandte Chemie International Edition. 2017 Oct 9;56(42):13117-13121. Epub 2017 Aug 29. doi: 10.1002/anie.201706804

Author

Barday, Manuel ; Janot, Christopher ; Halcovitch, Nathan R. et al. / Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds. In: Angewandte Chemie International Edition. 2017 ; Vol. 56, No. 42. pp. 13117-13121.

Bibtex

@article{fd79548c34f84866b3b7430102f2de52,
title = "Cross-Coupling of α-carbonyl sulfoxonium ylides with C-H bonds",
abstract = "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.",
keywords = "Sulfoxonium",
author = "Manuel Barday and Christopher Janot and Halcovitch, {Nathan R.} and James Muir and Christophe Aissa",
note = "This is the peer reviewed version of the following article: M. Barday, C. Janot, N. R. Halcovitch, J. Muir, C. A{\"i}ssa, 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.",
year = "2017",
month = oct,
day = "9",
doi = "10.1002/anie.201706804",
language = "English",
volume = "56",
pages = "13117--13121",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag",
number = "42",

}

RIS

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 -