Highly Regio- and Stereoselective Synthesis of Boron-Substituted Enynes via Copper-Catalyzed Borylation of Conjugated Diynes

被引：41

作者：

Li, DingXi

Kim, Yeong Eun

Yun, Jaesook ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

TERMINAL ALKYNES; COUPLING REACTIONS; HYDROBORATION; ALKENES; BIS(PINACOLATO)DIBORON; DIBORATION; 1,3-DIENES; ALLENES; DIBORON; ROUTE;

D O I：

10.1021/ol503720w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild copper-catalyzed regio- and stereoselective monoborylation of conjugated diynes with bis(pinacolato)diboron that affords enynylboronates is reported. The reaction is efficient for different types of conjugated diynes including unsymmetrical diynes and produces enynylboron compounds with high and complementary regioselectivity compared with classical hydrometalation reactions. In particular, the reactions of internal conjugated diynes with a silyl substitution produced highly functionalized enynes with high regio- and stereoselectivity, which can be used in further transformations.

引用

收藏

页码：860 / 863

页数：4

相关论文

共 50 条

[21] Visible Light-Induced Copper-Catalyzed Regio- and Stereoselective Difluoroalkylthiocyanation of Alkynes [J].

Hu, Xiaoxue ;

Wang, Yanzhao ;

Xu, Shibo ;

Wu, Jingjing ;

Wu, Fanhong .

JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12) :9118-9124

[22] Copper-Catalyzed Regio- and Stereoselective Oxidative Vinylsulfonylation of Quinoxalinones with Alkynes and Sulfonyl Hydrazides [J].

Clinton, Chayan Dhar ;

Prasad, Ch. Durga ;

Thombal, Raju S. ;

Lee, Yong Rok .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) :776-784

[23] Regio- and stereoselective copper-catalyzed α,β-protoboration of allenoates: access to Z-β,γ-unsaturated β-boryl esters [J].

Szwetkowski, Connor ;

Slebodnick, Carla ;

Santos, Webster L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (16) :3287-3291

[24] Highly regio- and stereoselective synthesis of 1,3-enynes from unactivated ethylenes via palladium-catalyzed cross-coupling [J].

Wen, Yanmei ;

Wang, Azhong ;

Jiang, Huanfeng ;

Zhu, Shifa ;

Huang, Liangbin .

TETRAHEDRON LETTERS, 2011, 52 (44) :5736-5739

[25] Copper-Catalyzed Regio- and Enantioselective Hydroboration of Difluoroalkyl-Substituted Internal Alkenes [J].

Zhao, Tao-Qian ;

Xu, Hui ;

Tian, Yu-Chen ;

Tang, Xiaodong ;

Dang, Yanfeng ;

Ge, Shaozhong ;

Ma, Jun-An ;

Zhang, Fa-Guang .

ADVANCED SCIENCE, 2023, 10 (35)

[26] Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes [J].

Itoh, Taisuke ;

Shimizu, Yohei ;

Kanai, Motomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (24) :7528-7531

[27] Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2 [J].

Gui, Yong-Yuan ;

Hu, Naifu ;

Chen, Xiao-Wang ;

Liao, Li-Li ;

Ju, Tao ;

Ye, Jian-Heng ;

Zhang, Zhen ;

Li, Jing ;

Yu, Da-Gang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (47) :17011-17014

[28] Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/ortho-Cyanation Cascade [J].

Yang, Yang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) :345-349

[29] Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols [J].

Mao, Lujia ;

Bertermann, Ruediger ;

Emmert, Katharina ;

Szabo, Kalman J. ;

Marder, Todd B. .

ORGANIC LETTERS, 2017, 19 (24) :6586-6589

[30] Copper-catalyzed protoboration of borylated dendralenes: a regio- and stereoselective access to functionalized 1,3-dienes [J].

Chaves-Pouso, Andrea ;

Rivera-Chao, Eva ;

Fananas-Mastral, Martin .

CHEMICAL COMMUNICATIONS, 2020, 56 (81) :12230-12233

← 1 2 3 4 5 →