Sulfanyl radical mediated cyclization of aminyl radicals

✍ Scribed by Pier Carlo Montevecchi; Maria Luisa Navacchia

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 237 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01998-4

✦ Synopsis

l-(2-Aminophenyl)pent-l-yne 1 reacted with benzenethiol at 150 °C under radical conditions to give the thiol/alkyne adduct 2, the benzothiophene 4 and the indole 5. Reaction of l with henzenesulfanyl radicals produced from diphenyl disulfide in the absence of hydrogen donors gave only the indole 5 in high yields. Formation of indole 5 was explained in terms of sulfanyl radical mediated aminyl radical cyclization onto the alkyne triple bond.