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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)

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Suzuki-Miyaura Cross-Coupling of Amides by N-C Cleavage Mediated by Air-Stable, Well-Defined [Pd(NHC)(sulfide)Cl2] Catalysts: Reaction Development, Scope, and Mechanism

S. Yang, X. Yu, Y. Liu, M. Tomasini, L. Caporaso, A. Poater, L. Cavallo, C. S. J. Cazin, S. P. Nolan, M. Szostak, J. Org. Chem., 2023, 88, 10858-10868.

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