Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.

Autor:	Kawamata Y; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Vantourout JC; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Hickey DP; Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Bai P; Department of Chemical Engineering and Materials Science , University of Minnesota , Minneapolis , Minnesota 55455 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Chen L; Asymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China., Hou Q; Asymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China., Qiao W; Asymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China., Barman K; Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Edwards MA; Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Garrido-Castro AF; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., deGruyter JN; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Nakamura H; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Knouse K; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Qin C; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Clay KJ; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Bao D; Asymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China., Li C; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Starr JT; Discovery Sciences, Medicine Design , Pfizer Global Research and Development , 445 Eastern Point Road , Groton , Connecticut 06340 , United States., Garcia-Irizarry C; Discovery Sciences, Medicine Design , Pfizer Global Research and Development , 445 Eastern Point Road , Groton , Connecticut 06340 , United States., Sach N; Department of Chemistry , La Jolla Laboratories, Pfizer , 10770 Science Center Drive , San Diego , California 92121 , United States., White HS; Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Neurock M; Department of Chemical Engineering and Materials Science , University of Minnesota , Minneapolis , Minnesota 55455 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Minteer SD; Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States., Baran PS; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.; Center for Synthetic Organic Electrochemistry , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2019 Apr 17; Vol. 141 (15), pp. 6392-6402. Date of Electronic Publication: 2019 Apr 02.
DOI:	10.1021/jacs.9b01886
Abstrakt:	C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.
Databáze:	MEDLINE
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