p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles

TETRAHEDRON

卷:66

Article

Jacubert, Maud¹  Provot, Olivier¹  Peyrat, Jean-Francois¹  Hamze, Abdallah¹  Brion, Jean-Daniel¹  Alami, Mouad¹ 

[1] Univ Paris Sud, CNRS, BioCIS, Chim Therapeut Lab,UMR 8076,Fac Pharm, F-92296 Chatenay Malabry, France

关键词: Alkynes;    Hydration;    p-Toluenesulfonic acid;    Ketone;    Benzofuran;    Benzothiophene;    Cyclization;   

DOI  :  10.1016/j.tet.2010.03.055

来源: Elsevier

【 摘 要 】

Regioselective hydration of a wide range of internal alkynes has been afforded in high to good yields by using PTSA in EtOH. The scope of the reaction of alkynes has been delineated. Arylaliphatic alkynes and diarylalkynes were regioselectively hydrated in good to excellent yields and short reaction times when the reaction was achieved under microwave irradiation. Moreover, diarylalkynes, arylenynes as well as diaryldiynes bearing a methoxy- or a thiomethyl substituent on the ortho position underwent a regioselective 5-endo-dig-cyclization to give a variety of 2-aryl- and 2-styrylbenzofuran or benzothiphene derivatives. We believe that, this new environmentally metal-free procedure combined to microwave irradiation would be in importance in the search of green laboratory-scale synthesis. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

Free