Hydrogen Bonding Cluster-Enabled Addition of Sulfonic Acids to Haloalkynes: Access to Both (E)- and (Z)-Alkenyl Sulfonates

被引：66

作者：

Zeng, Xiaojun ^{[1
]}

Liu, Shiwen ^{[1
]}

Shi, Zhenyu ^{[1
]}

Xu, Bo ^{[1
]}

机构：

[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED BROMOALKYNYLATION; TERMINAL ALKYNES; TOSYLATES; EFFICIENT; ENYNES; ARYL;

D O I：

10.1021/acs.orglett.6b02061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed an efficient synthesis of alkenyl sulfonates via hydrogen bonding cluster-enabled addition of sulfonic acids to haloalkynes. The reactivity of sulfonic acids could be significantly enhanced in the presence of strong hydrogen bonding donors. This metal-free method results in good chemical yields for a wide range of haloalkyne substrates and demonstrates good functional group tolerance. What is more, we can control the stereoselectivity of addition (cis vs trans) by varying the steric bulk of the sulfonic acid.

引用

页码：4770 / 4773

页数：4

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