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The Suzuki−Miyaura Coupling of Aryl Sulfones

preprint
revised on 07.05.2019, 15:04 and posted on 07.05.2019, 15:07 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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