Transition-metal-free borylation of propargylic alcohols: structurally variable synthesis in ionic liquid medium

被引:9
作者
Bhavanarushi, Sangepu [1 ]
Xu, Yin [1 ]
Khan, Imran [1 ]
Luo, Zhibin [1 ]
Liu, Bin [1 ]
Xie, Jimin [1 ]
机构
[1] Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 11期
关键词
N-HETEROCYCLIC CARBENES; FREE DIBORATION; B BOND; CATALYZED BORYLATION; CONJUGATE ADDITIONS; ALKYNES; TERTIARY; ACCESS; ESTERS; VINYL;
D O I
10.1039/c9qo00322c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Terminal or electron-deficient alkynes had been widely applied in transition-metal-free (TM-free) borylation with diboron reagents, allowing the construction of various vinylboronate reagents. By contrast, borylative addition to electronic unbiased triple bonds remained challenging in the TM-free approach. To address this issue, we developed base-promoted borylation of internal propargylic alcohols in ionic liquid medium affording structurally variable vinylboronates.
引用
收藏
页码:1895 / 1899
页数:5
相关论文
共 41 条
[11]   Allylic borylation of tertiary allylic alcohols: a divergent and straightforward access to allylic boronates [J].
Harada, Kohei ;
Nogami, Marina ;
Hirano, Keiichi ;
Kurauchi, Daisuke ;
Kato, Hisano ;
Miyamoto, Kazunori ;
Saito, Tatsuo ;
Uchiyama, Masanobu .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (05) :565-569
[12]   Diastereodivergent Synthesis of Trisubstituted Alkenes through Protodeboronation of Allylic Boronic Esters: Application to the Synthesis of the Californian Red Scale Beetle Pheromone [J].
Hesse, Matthew J. ;
Butts, Craig P. ;
Willis, Christine L. ;
Aggarwal, Varinder K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) :12444-12448
[13]   Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway [J].
Huang, Xi ;
Hu, Junjie ;
Wu, Mengying ;
Wang, Jiayi ;
Peng, Yanqing ;
Song, Gonghua .
GREEN CHEMISTRY, 2018, 20 (01) :255-260
[14]   Bis(imidazoline-2-thione)-copper(I) catalyzed regioselective boron addition to internal alkynes [J].
Kim, Hye Ryung ;
Jung, Il Gu ;
Yoo, Kihyun ;
Jang, Kwonho ;
Lee, Eun Sun ;
Yun, Jaesook ;
Son, Seung Uk .
CHEMICAL COMMUNICATIONS, 2010, 46 (05) :758-760
[15]   Direct and Base-Catalyzed Diboration of Alkynes Using the Unsymmetrical Diborane(4), pinB-BMes2 [J].
Kojima, Chiemi ;
Lee, Ka-Ho ;
Lin, Zhenyang ;
Yamashita, Makoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (20) :6662-6669
[16]   Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates [J].
Kuang, Zhijie ;
Chen, Haohua ;
Yan, Jianxiang ;
Yang, Kai ;
Lan, Yu ;
Song, Qiuling .
ORGANIC LETTERS, 2018, 20 (17) :5153-5157
[17]   Efficient C-B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls (vol 131, pg 7253, 2009) [J].
Lee, Kang-sang ;
Zhugralin, Adil R. ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (36) :12766-12766
[18]   Efficient C-B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls [J].
Lee, Kang-sang ;
Zhugralin, Adil R. ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (21) :7253-+
[19]   Generation and tandem reactions of 1-alkenyl-1,1-heterobimetallics: Practical and versatile reagents for organic synthesis [J].
Li, Hongimei ;
Carroll, Patrick J. ;
Walsh, Patrick J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3521-3531
[20]  
Malhotra S. V., 2007, ACS SYM SER, P72