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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

Peng Lei, Guangrong Meng, Yun Ling, Jie An, Steven P. Nolan and Michal Szostak*

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

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

DOI: 10.1021/acs.orglett.7b03191 (free Supporting Information)

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A combination of site-selective N,N-di-Boc-activation of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] enables a general, highly selective method for the room temperature Suzuki-Miyaura cross-coupling to provide biaryl ketones in high yields.

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

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

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.

Triflamides: Highly Reactive, Electronically Activated N-Sulfonyl Amides in Catalytic N-C(O) Amide Cross-Coupling

S. Shi, R. Lalancette, R. Szostak, M. Szostak, Org. Lett., 2019, 21, 1253-1257.

Key Words

aryl ketones, Suzuki coupling

ID: J54-Y2017