Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.
[reaction: see text] A wide variety of N-alkyl-3-iodoindoles are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization by I(2)(). Alkyl-, aryl-, and vinylic-substituted alkynes all undergo iodocyclization in excellent yields.
Yue
Dawei
D
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D000480:Alkynes; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000480:Alkynes; D000814:Aniline Compounds; D007211:Indoles; D010165:Palladium; D003300:Copper; C023650:aniline