Ligand-Controlled Copper-Catalyzed Regiodivergent Sulfonylation of Yne-Vinyl Allylic Esters with Sodium Sulfinates

被引：1

作者：

Zhu, Hui ^{[1
]}

Shen, Mingxin ^{[2
]}

Wang, Zi-Han ^{[1
]}

Huang, Genping ^{[2
]}

Lin, Tao-Yan ^{[1
]}

机构：

[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ,Anhui Prov Key Lab Synthet Chem & Appl, Huaibei 235000, Anhui, Peoples R China

[2] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China

来源：

ACS CATALYSIS | 2025年 / 15卷 / 03期

基金：

中国国家自然科学基金;

关键词：

copper; regioselectivity; yne-vinylallylicesters; copper divinyl-allenylidene complex; nucleophilicaddition; SUBSTITUTION-REACTIONS; SULFONES; ALKYLATION;

D O I：

10.1021/acscatal.4c07043

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Herein, we report the first ligand-controlled copper-catalyzed regiodivergent sulfonylation of yne-vinyl allylic esters with sodium sulfinates. The practicality and attractiveness of this protocol are showcased using readily available starting materials, mild reaction conditions, good regio- and stereoselectivities, and a broad substrate scope. A series of controlled experiments identified a copper divinyl-allenylidene complex as the key intermediate in this reaction. Density functional theory calculations delineate distinct mechanistic pathways for each nucleophilic addition step and elucidate their regioselectivity.

引用

页码：2415 / 2423

页数：9

共 46 条

[1] REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN SUBSTITUTION-REACTIONS OF CYCLOPHOSPHAZENES [J].