Application of a rhodium-catalyzed addition/cyclization sequence toward the synthesis of polycyclic heteroaromatics.
A cascade rhodium-catalyzed addition/cyclization reaction of bifunctional heteroromatic boronate esters to strained bicyclic alkenes has been developed. This method provides an efficient route to generate a variety of polycyclic heteroaromatic molecules containing benzothiophene, benzofuran, and indole moieties.
Tseng
Nai-Wen
NW
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
Lautens
Mark
M
D000475:Alkenes / Q000737:chemistry; D001572:Benzofurans / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry
D000475:Alkenes; D001572:Benzofurans; D001897:Boronic Acids; D004952:Esters; D006571:Heterocyclic Compounds; D007211:Indoles; D011083:Polycyclic Compounds; D013876:Thiophenes; C088015:benzothiophene; C030374:indole; D012238:Rhodium; C105430:benzofuran