Synthesis of 1,2-disubstituted acetylenes via copper-catalyzed Suzuki coupling of organoboronic acids with 1,1-dibromo-1-alkenes

An efficient synthesis of 1,2-disubstituted acetylenes has been described. Reactions of organoboronic acids with 1,1-dibromo-1-alkenes in the presence of a catalytic amount of CuI (10mol%), 8-hydroxyquinoline (10mol%), and using potassium phosphate as base in C2H5OH afforded the desired 1,2-disubsti...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2012-10, Vol.53 (42), p.5678-5683
Main Authors: Liu, Jidan, Dai, Fenglin, Yang, Zhiyong, Wang, Sizhuo, Xie, Kai, Wang, Anwei, Chen, Xiang, Tan, Ze
Format: Article
Language:English
Subjects:
1,1-Dibromo-1-alkene
1,2-Disubstituted acetylenes
Catalysis
Catalysts
Copper-catalyzed
Formations
Joining
Organoboronic acids
Potassium phosphates
Suzuki coupling
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient synthesis of 1,2-disubstituted acetylenes has been described. Reactions of organoboronic acids with 1,1-dibromo-1-alkenes in the presence of a catalytic amount of CuI (10mol%), 8-hydroxyquinoline (10mol%), and using potassium phosphate as base in C2H5OH afforded the desired 1,2-disubstituted acetylenes in good to excellent yields. It is important to note that the formation of 1,3-diynes, which are derived from the homocoupling of 1,1-dibromo-1-alkenes, can be almost completely suppressed under these optimized conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.08.044