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The Suzuki−Miyaura Coupling of Aryl Sulfones

preprint
revised on 07.05.2019 and posted on 07.05.2019 by Paul Chatelain, Abhijit Sau, Christopher Rowley, Joseph Moran
We describe conditions under which aryl sulfones act as electrophilic coupling partners in the palladium-catalyzed Suzuki–Miyaura cross-coupling (SMC) reaction. Sequential cross-coupling of arenes bearing sulfone, halide and nitro leaving groups permits rapid access to non-symmetric terphenyls and quaterphenyls starting from common functional groups. Mechanistic experiments and DFT calculations are consistent with oxidative addition into the sulfone C–S bond as the turnover-limiting step.

Funding

European Research Council (ERC) (grant agreement n° 639170)

ANR LabEx “Chemistry of Complex Systems” (ANR-10-LABX-0026 CSC)

NSERC Discovery Grant (application 418505-2012)

History

Email Address of Submitting Author

moran@unistra.fr

Institution

University of Strasbourg

Country

France

ORCID For Submitting Author

0000-0002-7851-6133

Declaration of Conflict of Interest

No conflict of interest.

Version Notes

This is version 2.

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