Enantioselective Synthesis of Axially Chiral Biaryls via Cu-Catalyzed Acyloxylation of Cyclic Diaryliodonium Salts

被引:86
作者
Zhu, Kai [1 ,2 ]
Xu, Kai [1 ]
Fang, Qi [1 ]
Wang, Yi [1 ]
Tang, Bencan [3 ]
Zhang, Fengzhi [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
[3] Univ Nottingham Ningbo China, Dept Chem & Environm Engn, Ningbo 315100, Zhejiang, Peoples R China
关键词
diaryliodonium salts; axially chiral biaryl; copper catalysis; acyloxylation; diversity oriented synthesis; DYNAMIC KINETIC RESOLUTION; ATROPOSELECTIVE SYNTHESIS; ATROPISOMERS; DERIVATIVES; CONSTRUCTION; LACTONES; LIGANDS; ALKYNES; ACIDS;
D O I
10.1021/acscatal.9b00695
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We report here a Cu-catalyzed enantioselective acyloxylation of cyclic diaryliodonium salts. With readily available cyclic diaryliodonium salts and ubiquitous aliphatic or (hetero)aromatic carboxylic acids as the starting materials, various axially chiral acyloxylated 2-iodobiaryls were prepared in excellent yield and with excellent enantioselectivity (mostly 99% yield and 99% ee). Density functional theory calculations were conducted to reveal the stereo- and regioselectivities. This simple reaction protocol can be employed for the late-stage modification of some drug molecules. Finally, by diversity-oriented transformations, these acyloxylated 2-iodobiaryl products can be easily transformed into diverse valuable functionalized biaryls that could be used as chiral ligands or functional materials.
引用
收藏
页码:4951 / 4957
页数:13
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