Palladium-catalyzed directing group assisted and regioselectivity reversed cyclocarbonylation of arylallenes with 2-iodoanilines
Literature Information
Publication Date
2020-12-07
DOI
10.1039/D0QO01404D
Impact Factor
5.281
Authors
Jian-Shu Wang, Lingyun Yao, Jun Ying, Xiaoling Luo
View Original
Abstract
A palladium-catalyzed regioselective cyclocarbonylation of N-(2-pyridyl)sulfonyl (N-SO2Py)-2-iodoanilines with allenes has been developed. With the assistance of the directing group N-SO2Py, the regioselectivity of arylallenes was reversed and the reaction proceeded well to give various 3-methylene-2,3-dihydroquinolin-4(1H)-ones with up to 95% yield by using benzene-1,3,5-triyl triformate (TFBen) as the CO source. Control experiments and DFT calculations were performed to understand the reaction details and a possible reaction mechanism is proposed accordingly.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
5-(3,4-Dimethoxybenzyl)-2,4-pyrimidinediamine hydrochloride (1:1)
CAS Number:
2507-23-5
Molecular Formula:
C13H17ClN4O2
tert-Butyl 4-(2-(p-Tolylsulfonyl)hydrazono)piperidine-1-carboxylate
CAS Number:
1046478-89-0
Molecular Formula:
C17H25N3O4S
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