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Synthesis 2019; 51(21): 4048-4065
DOI: 10.1055/s-0039-1690155
DOI: 10.1055/s-0039-1690155
paper
Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide
Financial support from the National Natural Science Foundation of China (51564021, 21762018 and 21772067), the Program of Qingjiang Excellent Young Talents, Jiangxi University of Science and Technology, and the Science and Technology Innovation Outstanding Young Talents Program of Jiangxi Province (20192BCBL23009) is gratefully acknowledged.Further Information
Publication History
Received: 21 June 2019
Accepted after revision: 23 July 2019
Publication Date:
14 August 2019 (online)

Abstract
The copper-catalyzed synthesis of 3-vinylisocoumarin-1-imine is reported. The transformation proceeds smoothly with good yields in THF and the regioselectivity was determined by a O-nucleophilic 6-endo cyclization. Studies on the mechanism indicate that copper trifluoroacetate serves as a Lewis acid, and the use of vinyl-connected 2-alkynylbenzamide is important for this O-nucleophilic 6-endo cyclization.
Key words
copper catalysis - O-nucleophilic 6-endo cyclization - Lewis acid - vinyl-connected 2-alkynylbenzamide - isocoumarinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690156.
- Supporting Information
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For selected reviews on dual-functionalized synthons, see:
For examples, see:
For 5-exo-dig N-attacked cyclization of o-alkynylbenzamide, see:
For selected examples of electrophilic cyclization, see:
For 6-endo-dig O-attacked cyclization of 2-alkynylbenzamide, see:
For transition-metal-catalyzed 5-exo-dig O-cyclization of 2-alkynylbenzamide, see:
For selected examples on cyclization under copper catalysis, see: