Iron-Catalyzed Cadiot-Chodkiewicz Coupling with High Selectivity in Water under Air
Journal
The Journal of organic chemistry
Journal Volume
87
Journal Issue
21
Date Issued
2022-11-04
Author(s)
Abstract
An iron-based catalytic system was developed for the cross-coupling of 1-bromoalkynes with terminal alkynes to selectively generate unsymmetrical 1,3-butadiynes in water under air. It was found that a combination of 1-bromoalkynes derived from less acidic terminal alkynes with more acidic counterparts would greatly enhance yields and selectivity for unsymmetrical 1,3-butadiynes. The reaction was also applicable for the synthesis of unsymmetrical 1,3,5-hexatriynes through coupling of 1-bromoalkynes and trimethylsilyl-protected 1,3-butadiynes in a one-pot manner.
Subjects
ONE-POT SYNTHESIS; TERMINAL ALKYNES; UNSYMMETRICAL 1,3-DIYNES; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE; IN-SITU; LIGAND; COPPER; 1-BROMOALKYNES; SYSTEM
Publisher
AMER CHEMICAL SOC
Type
journal article