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

Hirohiko Murase; Kousuke Senda; Masato Senoo; Takeshi Hata; Hirokazu Urabe

doi:10.1002/chem.201303008

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

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

Authors

Hirohiko Murase¹, Kousuke Senda, Masato Senoo, Takeshi Hata, Hirokazu Urabe

Affiliation

¹ 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.

PMID: 24302566
DOI: 10.1002/chem.201303008

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.

Keywords: chromene; dihydroquinolines; heterocycles; hydroarylation; rhodium.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Benzopyrans / chemical synthesis
Benzopyrans / chemistry
Catalysis
Coordination Complexes / chemistry
Heterocyclic Compounds / chemical synthesis
Heterocyclic Compounds / chemistry*
Hydrogenation
Quinolines / chemical synthesis
Quinolines / chemistry
Rhodium / chemistry*
Stereoisomerism

Substances

Alkynes
Benzopyrans
Coordination Complexes
Heterocyclic Compounds
Quinolines
Rhodium