Copper-Catalyzed Alkynylboration of Alkenes with Diboron Reagents and Bromoalkynes

被引：32

作者：

Gong, Tian-Jun ^{[1
]}

Yu, Shang-Hai ^{[1
]}

Li, Kuan ^{[1
]}

Su, Wei ^{[1
]}

Lu, Xi ^{[1
]}

Xiao, Bin ^{[1
]}

Fu, Yao ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Anhui Prov Key Lab Biomass Clean Energy, CAS Key Lab Urban Pollutant Convers,IChEM, Hefei 230026, Anhui, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2017年 / 12卷 / 22期

基金：

中国国家自然科学基金;

关键词：

boration; copper; cross-coupling; difunctionalization; synthetic methods; CROSS-COUPLING REACTIONS; COPPER(I)-CATALYZED REACTION; REGIOSELECTIVE ARYLBORATION; SONOGASHIRA REACTIONS; ALKYL ELECTROPHILES; C(SP(3))-H BONDS; HYDROBORATION; ARYL; HALIDES; ALKYNYLATION;

D O I：

10.1002/asia.201701176

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the synthesis of homopropargylboronates by copper-catalyzed alkynylboration of alkenes with diboron reagents and bromoalkynes has been developed. The alkynylboration reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional-group compatibility, and is a highly attractive complement to existing methods for the synthesis of homopropargylboronates. Both the boryl and alkynyl groups are good potential functional groups for the subsequent manipulations that provide access to a variety of important molecule structures.

引用

页码：2884 / 2888

页数：5

共 50 条

[1] Activation of diboron reagents: Catalytic copper-catalyzed borylation of electrophilic alkenes
Santos, Webster L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[2] Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents
Shen, Kun
Wang, Qiu
CHEMICAL SCIENCE, 2017, 8 (12) : 8265 - 8270
[3] Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents
Hirano, Koji
Miura, Masahiro
PURE AND APPLIED CHEMISTRY, 2014, 86 (03) : 291 - 297
[4] Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents
Bos, Pieter H.
Rudolph, Alena
Perez, Manuel
Fananas-Mastral, Martin
Harutyunyan, Syuzanna R.
Feringa, Ben L.
CHEMICAL COMMUNICATIONS, 2012, 48 (12) : 1748 - 1750
[5] Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with grignard reagents
Zhang, W
Wang, LX
Shi, WJ
Zhou, QL
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09): : 3734 - 3736
[6] Copper-catalyzed/mediated borylation reactions of epoxides with diboron reagents: access to β-hydroxyl boronic esters
Ahmed, Ebrahim-Alkhalil M. A.
Lu, Xi
Gong, Tian-Jun
Zhang, Zhen-Qi
Xiao, Bin
Fu, Yao
CHEMICAL COMMUNICATIONS, 2017, 53 (05) : 909 - 912
[7] Highly Enantioselective Copper-Catalyzed Ring Opening of Oxabicyclic Alkenes with Grignard Reagents
Zhang, Wei
Zhu, Shou-Fei
Qiao, Xiang-Chen
Zhou, Qi-Lin
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (12) : 2105 - 2111
[8] Copper-Catalyzed Enantioselective Arylalkynylation of Alkenes
Wu, Yan
He, Weimin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) : 2597 - 2599
[9] Copper-Catalyzed Oxyboration of Unactivated Alkenes
Itoh, Taisuke
Matsueda, Takumi
Shimizu, Yohei
Kanai, Motomu
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (45) : 15955 - 15959
[10] Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes
He, Yu-Tao
Li, Lian-Hua
Yang, Yan-Fang
Zhou, Zhao-Zhao
Hua, Hui-Liang
Liu, Xue-Yuan
Liang, Yong-Min
ORGANIC LETTERS, 2014, 16 (01) : 270 - 273

← 1 2 3 4 5 →