Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N−C Cleavage
Corresponding Author
Dr. Jin Zhang
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorPei Zhang
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorLei Shao
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorRuihong Wang
Institute of Frontier Science and Technology Transfer, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorYangmin Ma
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorCorresponding Author
Prof. Michal Szostak
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey, 07102 United States
Search for more papers by this authorCorresponding Author
Dr. Jin Zhang
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorPei Zhang
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorLei Shao
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorRuihong Wang
Institute of Frontier Science and Technology Transfer, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorYangmin Ma
College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an, Shaanxi, 710021 China
Search for more papers by this authorCorresponding Author
Prof. Michal Szostak
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey, 07102 United States
Search for more papers by this authorAbstract
Although cross-coupling reactions of amides by selective N−C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challenge. Herein, we report the first mechanochemical strategy for highly chemoselective, solvent-free palladium-catalyzed cross-coupling of amides by N−C bond activation. The method is conducted in the absence of external heating, for short reaction time and shows excellent chemoselectivity for σ N−C bond activation. The reaction shows excellent functional group tolerance and can be applied to late-stage functionalization of complex APIs and sequential orthogonal cross-couplings exploiting double solventless solid-state methods. The results extend mechanochemical reaction environments to advance the chemical repertoire of N−C bond interconversions to solid-state environmentally friendly mechanochemical methods.
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