Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 5, Pages 3234-3244Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03107
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Funding
- Novartis International AG
- National Institutes of Health [1F32GM113311]
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We report a visible light-mediated flow process for C-N cross-coupling of (hetero)aryl halides with a variety of amine coupling partners through the use of a photoredox/nickel dual catalyst system. Compared to the method in batch, this flow process enables a broader substrate scope, including less-activated (hetero)aryl bromides and electron-deficient (hetero)aryl chlorides, and significantly reduced reaction times (10 to 100 min). Furthermore, scale up of the reaction, demonstrated through the synthesis of tetracaine, is easily achieved, delivering the C-N cross-coupled products in consistently high yield of 84% on up to a 10 mmol scale.
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