Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides

Shaoyu Mai, Wendong Li, Xue Li, Yingwei Zhao and Qiuling Song ()
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Shaoyu Mai: College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University
Wendong Li: College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University
Xue Li: College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University
Yingwei Zhao: College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University
Qiuling Song: College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University

Nature Communications, 2019, vol. 10, issue 1, 1-12

Abstract: Abstract Cross-coupling reactions involving metal carbene intermediates play an increasingly important role in C–C bond formation. Expanding the carbene precursors to a broader range of starting materials and more diverse products is an ongoing challenge in synthetic organic chemistry. Herein, we report a Suzuki-Miyaura coupling reaction of in situ-generated Pd–carbene complexes via desulfurization of thioureas or thioamides. This strategy enables the preparation of a broad array of substituted amidinium salts and unsymmetrical diaryl ketones. The reaction is readily scalable, compatible with bromo groups on aromatic rings, tolerant to moisture and air and has a broad substrate scope. Furthermore, a single crystal structure of Pd-diaminocarbene complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions. Preliminary mechanistic studies demonstrate the dual role of the silver salt as a desulfurating reagent assisting the elimination of sulfur and as oxidant facilitating the PdII/Pd0/PdII catalytic cycle.

Date: 2019
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DOI: 10.1038/s41467-019-13701-5

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