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Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles

2013; Wiley; Volume: 20; Issue: 1 Linguagem: Inglês

10.1002/chem.201303008

1521-3765

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

Catalytic Cross-Coupling Reactions

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 Rh 2 (OCOCF 3 ) 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.