Solution-phase parallel synthesis of a multi-substituted benzo[b]thiophene library.
Generation of a library using parallel syntheses of multi-substituted benzo[b]thiophenes is described. The requisite 3-iodobenzo[b]thiophenes are readily prepared in excellent yields from various alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2) in CH(2)Cl(2). The heteroaromatic carbon-iodine bonds allow further diversification by palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, and carboalkoxylation chemistry to give multi-substituted benzo[b]thiophene derivatives.
Cho
Chul-Hee
CH
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Neuenswander
Benjamin
B
Lushington
Gerald H
GH
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D013876:Thiophenes; C088015:benzothiophene; D010165:Palladium