Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides.
- Resource Type
- Academic Journal
- Authors
- Fu J; Discovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.; Lundy W; Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Chowdhury R; Department of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.; Twitty JC; Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Dinh LP; Department of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.; Sampson J; High Throughput Experimentation Facility, Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Lam YH; Modeling & Informatics, Merck & Co., Inc., Rahway, New Jersey 07065, United States.; Sevov CS; Department of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.; Watson MP; Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Kalyani D; Discovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.
- Source
- Publisher: American Chemical Society Country of Publication: United States NLM ID: 101562209 Publication Model: Print-Electronic Cited Medium: Print ISSN: 2155-5435 (Print) NLM ISO Abbreviation: ACS Catal Subsets: PubMed not MEDLINE
- Subject
- Language
- English
- ISSN
- 2155-5435
An electrochemical, nickel-catalyzed reductive coupling of alkylpyridinium salts and aryl halides is reported. High-throughput experimentation (HTE) was employed for rapid reaction optimization and evaluation of a broad scope of pharmaceutically relevant structurally diverse aryl halides, including complex drug-like substrates. In addition, the transformation is compatible with both primary and secondary alkylpyridinium salts with distinct conditions. Mechanistic insights were critical to enhance the efficiency of coupling using secondary alkylpyridinium salts. Systematic comparisons of the electrochemical and non-electrochemical methods revealed the complementary scope and efficiency of the two approaches.