Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 20, Pages 13133-13140Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01816
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Funding
- Ministerio de Ciencia e Innovacion (MCI/AEI/FEDER, UE) [RTI2018-093721-B-I00]
- Basque Government [IT1033-16, IT1254-19]
- European funding (ERDF)
- European funding (ESF)
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Despite the widespread use of cross-dehydrogenative couplings in modern organic synthesis, mechanistic studies are still rare in the literature and those applied to alpha-amino carbonyl compounds remain virtually unexplored. Herein, the mechanism of Co-catalyzed cross-dehydrogenative couplings of N-aryl glycinates with indoles is described. Density functional theory studies supported the formation of an imine-type intermediate as the more plausible transient electrophilic species. Likewise, key information regarding the role of the N-aryl group and free NH motif within the reaction outcome has been gained, which may set the stage for further developments in this field of expertise.
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