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

Peng Lei, Guangrong Meng, Yun Ling, Jie An and Michal Szostak*

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

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

DOI: 10.1021/acs.joc.7b00749 (free Supporting Information)

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Abstract

An array of amides can be cross-coupled with a range of arylboronic acids in very good yields using a commercially available, air- and moisture-stable Pd-PEPPSI-IPr complex as a highly reactive precatalyst in a single, operationally simple protocol. Pd-PEPPSI-IPr provides a significant improvement over all current Pd/phosphane catalysts for amide N-C bond activation.

see article for more examples

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Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions

Md. M. Rahman, D. J. Pyle, E. Bisz, B. Dziuk, K. Ejsmont, R. Lalancette, Q. Wang, H. Chen, R. Szostak, M. Szostak, J. Org. Chem., 2021, 86, 10455-10466.

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.

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

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

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.

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Key Words

Suzuki coupling, ketones

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ID: J42-Y2017