铑催化的 1-卤代-1-炔烃的分子内氢芳基化反应：区域选择性合成半氢化芳杂环。

Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles.

机构信息

Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501 (Japan), Fax: (+81) (0)45-924-5849.

出版信息

Chemistry. 2014 Jan 3;20(1):317-22. doi: 10.1002/chem.201303008. Epub 2013 Dec 2.

DOI:10.1002/chem.201303008

PMID:24302566

Abstract

The regioselective intramolecular hydroarylation of (3-halo-2-propynyl)anilines, (3-halo-2-propynyl) aryl ethers, or (4-halo-3-butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4-halo-1,2-dihydroquinolines, 4-halo-3-chromenes, or 4-(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo-substituents of the products are also illustrated.

摘要

（3-卤代-2-丙炔基）苯胺、（3-卤代-2-丙炔基）芳基醚或（4-卤代-3-丁炔基）芳基醚的区域选择性分子内氢芳基化反应，可通过 Rh2(OCOCF3)4 高效催化，得到半氢化芳香杂环化合物，如 4-卤代-1,2-二氢喹啉、4-卤代-3-色烯或 4-（卤亚甲基）色满，产率良好至优秀。还说明了一些利用产物中卤原子取代基的合成应用。