Iron Halide-Mediated Regio- and Stereoselective Halosulfonylation of Terminal Alkynes with Sulfonylhydrazides: Synthesis of (E)-β-Chloro and Bromo Vinylsulfones

被引：124

作者：

Li, Xiaoqing ^{[1
]}

Shi, Xinhua ^{[1
]}

Fang, Mingwu ^{[1
]}

Xu, Xiangsheng ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 18期

基金：

中国国家自然科学基金;

关键词：

CATALYZED ALLYLIC SULFONYLATION; BETA-CHLOROVINYL SULFONES; CROSS-COUPLING REACTIONS; HALOGEN-METAL EXCHANGE; VINYL SULFONES; CHLORIDES; ACETYLENES; ALKENES; DIFUNCTIONALIZATION; DERIVATIVES;

D O I：

10.1021/jo401581n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halosulfonylation of terminal alkynes was achieved with sulfonylhydrazides as the sulfonyl precursor and inexpensive iron halide as halide source in the presence TBHP, allowing the regio- and stereoselective generation of (E)-beta-chloro and bromo vinylsulfones.

引用

页码：9499 / 9504

页数：6

共 36 条

[1] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[2]

AMIEL Y, 1971, J ORG CHEM, V36, P3691, DOI 10.1021/jo00823a007

[3]

AMIEL Y, 1971, TETRAHEDRON LETT, P661

[4] ADDITION OF SULFONYL CHLORIDES TO ACETYLENES .2. STEREOSELECTIVE CONTROL IN SYNTHESES OF BETA-CHLOROVINYL SULFONES [J].

AMIEL, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (24) :3697-&

[5] THERMAL AND COPPER-CATALYZED ADDITION OF SULFONYL BROMIDES TO PHENYLACETYLENE [J].

AMIEL, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (26) :3867-3870

[6] Halogen-metal exchange in 1,2-dibromobenzene and the possible intermediacy of 1,2-dilithiobenzene [J].

Bettinger, Holger F. ;

Filthaus, Matthias .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9750-9752

[7] General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans.: Efficient synthesis of an anti-inflammatory gorgonian lipid [J].

Boukouvalas, John ;

Loach, Richard P. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :8109-8112

[8] Cobalt-Catalyzed Cross-Coupling Reactions [J].

Cahiez, Gerard ;

Moyeux, Alban .

CHEMICAL REVIEWS, 2010, 110 (03) :1435-1462

[9] Silver-Catalyzed Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates [J].

Chen, Zhengwang ;

Li, Jinghao ;

Jiang, Huanfeng ;

Zhu, Shifa ;

Li, Yibiao ;

Qi, Chaorong .

ORGANIC LETTERS, 2010, 12 (14) :3262-3265

[10] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

← 1 2 3 4 →