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1,1-二溴乙烯与炔基铝的高选择性交叉偶联反应用于合成芳基取代的共轭烯二炔和不对称1,3-二炔。

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

作者信息

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

机构信息

Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University Chengdu 610041 P. R. China

出版信息

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

DOI:10.1039/d2ra02127g
PMID:35520111
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9062886/
Abstract

A highly efficient method for the synthesis of aryl substituted conjugated enediynes and unsymmetrical 1,3-diynes selective cross-coupling reactions of 1,1-dibromoethylenes with alkynylaluminums using the Pd(OAc)-DPPE and Pd(dba)-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.

摘要

分别使用Pd(OAc)-DPPE和Pd(dba)-TFP配合物作为催化剂,通过1,1-二溴乙烯与炔基铝的选择性交叉偶联反应,成功开发了一种高效合成芳基取代共轭烯二炔和不对称1,3-二炔的方法。虽然未得到烷基取代的共轭烯二炔和不对称1,3-二炔,但这种情况也很显著,因为相同的起始原料在不同的钯-膦催化体系中能够以中等至优异的产率(高达99%)选择性地生成芳基取代的共轭烯二炔或不对称1,3-二炔。

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