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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. Mahbubur Rahman, Daniel J. Pyle, Elwira Bisz, Błażej Dziuk, Krzysztof Ejsmont, Roger Lalancette, Qi Wang, Hao Chen, Roman Szostak and Michal Szostak*

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

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.

DOI: 10.1021/acs.joc.1c01110 (free Supporting Information)


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Abstract

Evaluation of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings using Pd(II)-NHC and Pd-phosphine systems has revealed the relative reactivity order of N-activating groups in Suzuki-Miyaura cross-coupling. N-Acyl-δ-valerolactams are highly effective precursors for cross-coupling via acyl-metal intermediates.

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[(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions

Q. Xia, S. Shi, P. Gao, R. Lalancette, R. Szostak, M. Szostak, J. Org. Chem., 2021, 86, 15650-15657.

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.


Key Words

aryl ketones, Suzuki coupling


ID: J42-Y2021