A Four-Component Cascade C-H Functionalization/Cyclization/Nucleophilic Substitution Reaction To Construct α-Functionalized Tetrahydroquinolines by the Strategy of in Situ Directing Group Formation

A four-component cascade C-H functionalization/cyclization/nucleophilic substitution reactions of anilines, carboxylic anhydrides, propenol, and alkohols have been developed by a strategy of in situ directing group formation, affording an efficient and convenient synthesis of α-alkoxyl tetrahydroqui...

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Bibliographic Details
Published in:Organic letters 2017-03, Vol.19 (6), p.1374-1377
Main Authors: Bai, Peng, Li, Ya-Qiong, Huang, Zhi-Zhen
Format: Article
Language:English
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Summary:A four-component cascade C-H functionalization/cyclization/nucleophilic substitution reactions of anilines, carboxylic anhydrides, propenol, and alkohols have been developed by a strategy of in situ directing group formation, affording an efficient and convenient synthesis of α-alkoxyl tetrahydroquinolines from basic starting materials. A plausible mechanism involving rhodium(III) catalytic C-H functionalization and double nucleophilic attacks is proposed. The nucleophilicity order of some alcohols is also obtained for the cascade reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00226