Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.
[reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.
Zhang
Xiaoxia
X
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Sarkar
Sampa
S
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004583:Electrons; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D009281:Naphthalenes; D009284:Naphthols