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Sterically Controlled Pd-Catalyzed Chemoselective Ketone Synthesis via N-C Cleavage in Twisted Amides

Guangrong Meng and Michal Szostak*

*Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States, Email:

G. Meng, M. Szostak, Org. Lett., 2015, 17, 4364-4367.

DOI: 10.1021/acs.orglett.5b02209 (free Supporting Information)

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A highly chemoselective, palladium(0)-catalyzed, direct cross-coupling between boronic acids and geometrically activated amides shows excellent functional group tolerance, and delivers the versatile ketone products in high yields. Notably, the method provides direct access to acyl-metal intermediates from sterically distorted, bench-stable amide precursors under mild catalytic conditions.

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General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature

P. Lei, G. Meng, Y. Ling, J. An, S. P. Nolan, M. Szostak, Org. Lett., 2017, 19, 6510-6513.

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

P. Lei, G. Meng, Y. Ling, J. An, M. Szostak, J. Org. Chem., 2017, 82, 6638-6646.

Key Words

ayl ketones

ID: J54-Y2015