Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 15648-15657Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02183
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Funding
- Rutgers University
- NIH [1R35GM133326]
- NSF [CAREER CHE-1650766]
- ACS PRF [DNI-55549]
- Rutgers University -Newark Chancellor's Research Office
- Wroclaw Center for Networking and Supercomputing [WCSS159]
- National Natural Science Foundation of China [21602159]
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This study reports the synthesis, characterization, and reactivity of [(NHC)PdCl2(aniline)] complexes, which are highly active catalysts in various Suzuki-Miyaura reactions. The introduction of broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts has significant potential in fine-tuning challenging cross-coupling reactions. The commercialization of the parent catalyst [Pd(IPr)(AN)Cl-2] offers broad access for reaction screening and optimization.
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)Cl-2], has been commercialized in collaboration with Millipore Sigma, offering broad access for reaction screening and optimization.
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