On the Mechanism of Cross-Dehydrogenative Couplings between N-aryl Glycinates and Indoles: A Computational Study

被引：17
作者：
Andrade-Sampedro, Paula [1 ,2 ]
Correa, Arkaitz [1 ]
Matxain, Jon M. [2 ,3 ]
机构：
[1] Univ Basque Country UPV EHU, Dept Organ Chem 1, Joxe Mari Korta R&D Ctr, Donostia San Sebastian 20018, Spain
[2] Donostia Int Phys Ctr DIPC, Donostia San Sebastian 20018, Spain
[3] Euskal Herriko Unibertsitatea UPV EHU, Polimero & Mat Aurreratuak Fis Kimika & Teknol Sa, Kimika Fak, Donostia San Sebastian 20018, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 20期
关键词：
AMINO CARBONYL-COMPOUNDS; DIRECT ALPHA-ARYLATION; C-H FUNCTIONALIZATION; COBALT(II)-CATALYZED DECOMPOSITION; BONDS; ACID; ABSTRACTION; DERIVATIVES; HYDROPEROXIDE; CATALYSIS;
D O I：
10.1021/acs.joc.0c01816
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：13133 / 13140
页数：8
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