Iron-Catalyzed Cadiot–Chodkiewicz Coupling with High Selectivity in Water under Air
Yi-An Liao, Wen‐Sheng Peng, Lingjun Liu, Ting-You Ye, Jun‐Hao Fu, Yi‐Tsu Chan, Fu‐Yu Tsai
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.
Topics & Concepts
SelectivityCatalysisCoupling (piping)ChemistryCombinatorial chemistryTerminal (telecommunication)Coupling reactionOrganic chemistryMaterials scienceMetallurgyComputer scienceTelecommunicationsCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions