Highly selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes

Kun Wu; Chuan Wu; Xiao-Ying Jia; Lin Zhou; Qing-Han Li

doi:10.1039/d2ra02127g

Highly selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes

RSC Adv. 2022 May 3;12(21):13314-13318. doi: 10.1039/d2ra02127g. eCollection 2022 Apr 28.

Authors

Kun Wu¹, Chuan Wu¹, Xiao-Ying Jia¹, Lin Zhou¹, Qing-Han Li¹

Affiliation

¹ Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University Chengdu 610041 P. R. China zhoulin@swun.edu.cn.

Abstract

A highly efficient method for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes via selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums using the Pd(OAc)₂-DPPE and Pd₂(dba)₃-TFP complexes as catalysts, respectively, has been successfully developed. Though the alkyl substituted conjugated enediynes and unsymmetrical 1,3-diynes were not obtained, this case is also remarkable as the same starting materials could selectively produce either aryl substituted conjugated enediynes or unsymmetrical 1,3-diynes in moderate to excellent yields (up to 99%) in the different Pd-phosphine catalytic systems.