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

Qinqin Xia, Shicheng Shi, Pengcheng Gao, Roger Lalancette, Roman Szostak and Michal Szostak*

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

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

DOI: 10.1021/acs.joc.1c02183

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Abstract

The commercially available [(IPr)PdCl2(aniline)] complex is a well-defined, air- and moisture-stable catalyst for highly efficient Suzuki-Miyaura cross-coupling of amides, esters, aryl chlorides, and Buchwald-Hartwig amination. The availability of various aniline scaffolds has a significant potential in fine-tuning of challenging cross-couplings by Pd-NHCs.


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direct synthesis of (IPr)PdCl2(AN)

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.

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.

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

aryl ketones, Suzuki coupling

ID: J42-Y2021