TY - JOUR
T1 - Complexes
T2 - Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions
AU - Xia, Qinqin
AU - Shi, Shicheng
AU - Gao, Pengcheng
AU - Lalancette, Roger
AU - Szostak, Roman
AU - Szostak, Michal
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/11/5
Y1 - 2021/11/5
N2 - We report the synthesis, characterization, and reactivity of [(NHC)PdCl2(aniline)] complexes. These well-defined, air- and moisture-stable catalysts are highly active in the Suzuki-Miyaura cross-coupling of amides by N-C(O) activation as well as in the Suzuki-Miyaura cross-coupling of esters, aryl chlorides, and Buchwald-Hartwig amination. Most crucially, this study introduces broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts. The availability of various aniline scaffolds, including structural and electronic diversity, has a significant potential in fine-tuning of challenging cross-couplings by Pd-NHCs. The parent catalyst in this class, [Pd(IPr)(AN)Cl2], has been commercialized in collaboration with Millipore Sigma, offering broad access for reaction screening and optimization.
AB - We report the synthesis, characterization, and reactivity of [(NHC)PdCl2(aniline)] complexes. These well-defined, air- and moisture-stable catalysts are highly active in the Suzuki-Miyaura cross-coupling of amides by N-C(O) activation as well as in the Suzuki-Miyaura cross-coupling of esters, aryl chlorides, and Buchwald-Hartwig amination. Most crucially, this study introduces broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts. The availability of various aniline scaffolds, including structural and electronic diversity, has a significant potential in fine-tuning of challenging cross-couplings by Pd-NHCs. The parent catalyst in this class, [Pd(IPr)(AN)Cl2], has been commercialized in collaboration with Millipore Sigma, offering broad access for reaction screening and optimization.
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U2 - 10.1021/acs.joc.1c02183
DO - 10.1021/acs.joc.1c02183
M3 - Article
AN - SCOPUS:85117516720
SN - 0022-3263
VL - 86
SP - 15648
EP - 15657
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -