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Journal Article

Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58636

Huang,  Xueliang
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58872

Patil,  Mahendra
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58537

Farès,  Christophe
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons59045

Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58809

Maulide,  Nuno
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

ja4017683_si_001.pdf
(Supplementary material), 3MB

Citation

Huang, X., Patil, M., Farès, C., Thiel, W., & Maulide, N. (2013). Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds. Journal of the American Chemical Society, 135(19), 7312-7323. doi:10.1021/ja4017683.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A366-B
Abstract
The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.