Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N‑Heteroarenes

Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxy­phthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyr...

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Published inOrganic letters Vol. 21; no. 14; pp. 5728 - 5732
Main Authors Lyu, Xue-Li, Huang, Shi-Sheng, Song, Hong-Jian, Liu, Yu-Xiu, Wang, Qing-Min
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IRIDIUM COMPLEXES
ALKYLATION
PHOTOCATALYSIS
PHOTOPOLYMERIZATION
ALDEHYDES
N-(ACYLOXY)PHTHALIMIDE
TRANSFORMATIONS
CYCLIZATION
PHOTOREDOX CATALYSIS
CARBOXYLIC-ACIDS
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Summary:Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxy­phthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu­(dmp)­(xantphos)]­BF4.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02105