Metal-Free Synthesis of ortho-CHO Diaryl Ethers by a Three-Component Sequential Coupling

被引：33
|
作者：
Liu, Fangliang [1 ]
Yang, Huameng [2 ]
Hu, Xinquan [1 ,2 ]
Jiang, Gaoxi [2 ,3 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[3] Chinese Acad Sci, Suzhou Inst Nanotech & Nanobion, Suzhou 215123, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 24期
关键词：
O BOND FORMATION; ARYL ETHERS; DIARYLIODONIUM SALTS; ALKYL-ARYL; ARYNES; COPPER; INSERTION; ARYLATION; PHENOLS; MILD;
D O I：
10.1021/ol503224u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical, metal-free, and highly chemoselective approach was developed for the synthesis of ortho-CHO diaryl ethers by a three-component sequential coupling of arynes, N,N-dimethylformamide (DMF), and diaryliodonium salts. Diverse functional groups including halo, nitryl, and bulky substituents and heteroaromatics are well tolerated. Mechanistically, isotopic tracer experiments reveal that the diaryliodonium salt serves as an electrophile to trap the transient intermediates generated from the [2 + 2] cyclization of an aryne and DMF.
引用
收藏
页码：6408 / 6411
页数：4
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