Copper-Catalyzed Regioselective Formal Allylboration of Aryl-Substituted Terminal Alkynes with Bis(pinacolato)diboron and Allyl Halides/Sulfonates

被引：11

作者：

Jing, Haitong ^{[1
]}

Feng, Xiaorui ^{[1
]}

Guo, Minjie ^{[2
]}

Zhou, Sen ^{[1
]}

Li, Yanlin ^{[1
]}

Zhang, Jiacheng ^{[3
]}

Zhao, Wentao ^{[1
]}

Tang, Xiangyang ^{[1
]}

Wang, Guangwei ^{[1
]}

机构：

[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China

[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, Inst Mol Design & Synth, Tianjin 300072, Peoples R China

[3] Tianjin Med Univ, Sch Pharm, Tianjin 300070, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 10期

关键词：

1,4-dienes; alkenylboron compounds; allylation; boron; copper; STEREOSELECTIVE-SYNTHESIS; CARBOBORATION; ALKENES; DERIVATIVES; ALKYLATION; BORYLATION; ACETYLENES; 1,4-DIENES; ESTERS; ACIDS;

D O I：

10.1002/ajoc.201700263

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed formal allylboration of terminal alkynes using allyl bromides or sulfonates as electrophiles has been achieved. This method exhibits good regio-/stereoselectivity and good functional-group tolerance for various substituents on the aromatic rings of arylethynes. Through this strategy, various trisubstituted vinyl pinacol boronic esters with a 1,4-diene skeleton have been constructed. In order to demonstrate the utility of this method, the resulting 1,4-dienes with boron substitution were further used in transformations such as Suzuki coupling, oxidation, halogenation, and so on, leading to various important compounds.

引用

页码：1375 / 1379

页数：5

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