Copper-catalyzed borylative cyclization of 1,n-enynyl phosphates leading to five- to eight-membered cyclic 1,4-dienyl boronates

被引：15

作者：

Zhang, Fang ^{[1
]}

Wang, Shuaifeng ^{[1
]}

Liu, Zhicheng ^{[1
]}

Bai, Yihui ^{[1
]}

Zhu, Gangguo ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem, 688 Yingbin Rd, Jinhua 321004, Peoples R China

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 15期

基金：

中国国家自然科学基金;

关键词：

Copper; Enyne; Allylboration; Cyclization; 1,4-Dienyl boronates; ALLYL PHOSPHATES; INTRAMOLECULAR CYANOBORATION; STEREOSELECTIVE-SYNTHESIS; ANTI-CARBOBORATION; ALKYNES; 1,6-ENYNES; LIGAND; PD; ALKENYL; BIS(PINACOLATO)DIBORON;

D O I：

10.1016/j.tetlet.2017.02.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here a room temperature, efficient, and broadly applicable copper-catalyzed borylative cyclization of 1,n-enynyl (n = 6-9) phosphates for the concise synthesis of structurally diverse 5-8 membered cyclic 1,4-dienyl boronates, which represents the first Cu-catalyzed formal intramolecular alkyne allylboration. Subsequent Suzuki-Miyaura coupling provides a facile access to cyclized 1,4-dienes. A mechanism consisting of alkyne borylcupration, intramolecular alkene addition, and 8-elimination has been proposed to explain the experimental results. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1448 / 1452

页数：5

共 51 条

[31] Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Unactivated Terminal Alkynes [J].

Su, Wei ;

Gong, Tian-Jun ;

Zhang, Qi ;

Zhang, Qing ;

Xiao, Bin ;

Fu, Yao .

ACS CATALYSIS, 2016, 6 (10) :6417-6421

[32] Intramolecular cyanoboration of alkynes via activation of boron-cyanide bonds by transition metal catalysts [J].

Suginome, M ;

Yamamoto, A ;

Murakami, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (23) :5300-5308

[33] Palladium- and nickel-catalyzed intramolecular cyanoboration of alkynes [J].

Suginome, M ;

Yamamoto, A ;

Murakami, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6358-6359

[34] Nickel-catalyzed addition of alkynylboranes to alkynes [J].

Suginome, Michinori ;

Shirakura, Masamichi ;

Yamamoto, Akihiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) :14438-14439

[35] Reactions of cyanoboranes with a palladium-PMe3 complex:: Mechanism for the catalytic cyanoboration of alkynes [J].

Suginome, Michinori ;

Yamamoto, Akihiko ;

Sasaki, Taisuke ;

Murakami, Masahiro .

ORGANOMETALLICS, 2006, 25 (12) :2911-2913

[36] Rhodium-Catalyzed Asymmetric Arylation [J].

Tian, Ping ;

Dong, Han-Qing ;

Lin, Guo-Qiang .

ACS CATALYSIS, 2012, 2 (01) :95-119

[37] Asymmetric conjugate alkenylation of enones catalyzed by chiral diols [J].

Wu, T. Robert ;

Chong, J. Michael .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :4908-+

[38] Cobalt-Catalyzed Ligand-Controlled Regioselective Hydroboration/Cyclization of 1,6-Enynes [J].

Xi, Tuo ;

Lu, Zhan .

ACS CATALYSIS, 2017, 7 (02) :1181-1185

[39] Silaborative Carbocyclizations of 1,7-Enynes. Diastereoselective Preparation of Chromane Derivatives [J].

Xiao, You-Cai ;

Moberg, Christina .

ORGANIC LETTERS, 2016, 18 (02) :308-311

[40] Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond [J].

Yamamoto, A ;

Suginome, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15706-15707

← 1 2 3 4 5 6 →