| Literature DB >> 30905151 |
Yu Kawamata1,2, Julien C Vantourout1, David P Hickey3,2, Peng Bai4,2, Longrui Chen5, Qinglong Hou5, Wenhua Qiao5, Koushik Barman3,2, Martin A Edwards3,2, Alberto F Garrido-Castro1, Justine N deGruyter1, Hugh Nakamura1, Kyle Knouse1, Chuanguang Qin1, Khalyd J Clay1, Denghui Bao5, Chao Li1, Jeremy T Starr6, Carmen Garcia-Irizarry6, Neal Sach7, Henry S White3,2, Matthew Neurock4,2, Shelley D Minteer3,2, Phil S Baran1,2.
Abstract
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.Entities:
Year: 2019 PMID： 30905151 PMCID： PMC6996791 DOI： 10.1021/jacs.9b01886
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419