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

被引：13
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
收藏
页码：1448 / 1452
页数：5
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