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Ligand-Enabled, Palladium-Catalyzed Beta-C (sp3)–H Arylation of Weinreb Amides

preprint
submitted on 05.07.2018 and posted on 06.07.2018 by Hojoon Park, Nikita Chekshin, Peng-Xiang Shen, jin-quan yu

We report the development of Pd(II)-catalyzed C(sp3)–H arylation of Weinreb amides. A pyridinesulfonic acid ligand is designed to accommodate the weak, neutral coordinating property of Weinreb amides via preserving the cationic character of Pd center through zwitterionic assembly of Pd/ligand complexes. DFT studies of the C–H cleavage step indicate that the superior reactivity of 3-pyridinesulfonic acid ligand compared to pyridine, Ac-Gly-OH, and ligandless conditions originates from the stabilization of overall substrate-bound Pd species.

Funding

NIGMS, 2R01GM084019

History

Email Address of Submitting Author

yu200@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-3560-5774

Declaration of Conflict of Interest

no conflict of interest

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