Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.
[reaction: see text] 2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, or p-O2NC6H4SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in excellent yields. Biologically important furopyridines can be prepared by this approach in high yields.
Yue
Dawei
D
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Yao
Tuanli
T
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry; D000840:Anisoles / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry
D000480:Alkynes; D000840:Anisoles; D001572:Benzofurans; D010165:Palladium