Copper-catalyzed boroacylation of allenes to access tetrasubstituted vinylboronates

被引：6
作者：
Shen, Bing-Xue [1 ,2 ]
Min, Xiang-Ting [1 ,2 ]
Hu, Yan-Cheng [1 ]
Qian, Lei-Lei [1 ,2 ]
Yang, Sa-Na [1 ,2 ]
Wan, Boshun [1 ]
Chen, Qing-An [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 45期
基金：
中国国家自然科学基金;
关键词：
C-H ACTIVATION; STEREOSELECTIVE-SYNTHESIS; BORYLATIVE CYCLIZATION; PALLADIUM COMPLEXES; EFFICIENT ROUTE; ALKYNES; HYDROBORATION; CARBOBORATION; ALKENES; BORYLCUPRATION;
D O I：
10.1039/d0ob02008g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A distinct copper-catalyzed boroacylation of allenes with acyl chlorides and bis(pinacolato)diboron is developed. For aromatic acyl chlorides, 1,2-boroacylation of allenes readily takes place, leading to the formation of tetrasubstituted vinylboronates with exclusive (E)-stereoselectivity. In comparison, the employment of alkyl acyl chlorides as electrophiles alters the selectivity to 2,3-boroacylated products. Additionally, the product can easily undergo Suzuki-Miyaura cross-coupling to afford tetrasubstituted alkene with complete retention of the configuration.
引用
收藏
页码：9253 / 9260
页数：8
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