Authors
- Yu Kawamata ,
- Julien Vantourout ,
- David P. Hickey ,
- Peng Bai ,
- Longrui Chen ,
- Qinglong Hou ,
- Wenhua Qiao ,
- Koushik Barman ,
- Martin A. Edwards ,
- Alberto F. Garrido-Castro ,
- Justine N. deGruyter ,
- Hugh Nakamura ,
- Kyle W. Knouse ,
- Chuanguang Qin ,
- Khalyd J. Clay ,
- Denghui Bao ,
- Chao Li ,
- Jeremy T. Starr ,
- Carmen N. Garcia-Irizarry ,
- Neal Sach ,
- Henry S. White ,
- Matthew Neurock ,
- Shelley D. Minteer ,
- Phil Baran
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The Scripps Research Institute
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 as well as procedures for both batch and flow scale-ups (100 gram) are also described.
Content
Supplementary material
