Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Amides

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Amides
Yun Ling, Jie An, Michal Szostak, Peng Lei, Guangrong Meng
Pd-PEPPSI-IPr serves as a highly reactive precatalyst in the direct Suzuki–Miyaura cross-coupling of amides. An array of amides can be cross-coupled with a range of arylboronic acids in very good yields using a single, operationally simple protocol. The studies described represent the first use of versatile PEPPSI type of Pd-NHC complexes as catalysts for the cross-coupling of amides by N–C bond activation. The method is user-friendly, since it employs a commercially available, air- and moisture-stable Pd-PEPPSI-IPr complex. Pd-PEPPSI-IPr provides a significant improvement over all current Pd/phosphane catalysts for amide N–C bond activation. Mechanistic studies provide insight into the reaction rates of Pd-NHC-catalyzed cross-coupling of different amides, with Pd-PEPPSI-IPr being particularly effective for the cross-coupling of N-Boc carbamates under the developed conditions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00749

DOI: 10.1021/acs.joc.7b00749

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