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Photoinduced Copper‐Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides
Author(s) -
Hazra Avijit,
Lee Mitchell T.,
Chiu Justin F.,
Lalic Gojko
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201801085
Subject(s) - chemistry , electrophile , alkyl , alkylation , aryl , catalysis , ketone , amide , nitrile , polymer chemistry , epoxide , photochemistry , organic chemistry
We have developed a photoinduced copper‐catalyzed alkylation of terminal alkynes with primary, secondary, or tertiary alkyl iodides as electrophiles. The reaction has a broad substrate scope and can be successfully performed in the presence of ester, nitrile, aryl halide, ketone, sulfonamide, epoxide, alcohol, and amide functional groups. The alkylation is promoted by blue light ( λ ≈450 nm) and proceeds at room temperature in the absence of any additional metal catalysts. The use of a terpyridine ligand is essential for the success of the reaction and is shown to prevent photoinduced copper‐catalyzed polymerization of the starting materials.