Modular construction of 2-substituted benzo[b]furans from 1,2-dichlorovinyl ethers.
(E)-1,2-Dichlorovinyl ethers and amides are easily accessible from trichloroethylene via nucleophilic addition across in situ synthesized dichloroacetylene. A one-pot, sequential Suzuki-Miyaura coupling/intramolecular direct arylation between dichlorovinyl ethers and organoboronic acids provides easy access to a variety of benzofurans in only two steps from inexpensive commercially available compounds. The method is extendable to the preparation of indoles from the analogous dichlorovinyl amides.
Geary
Laina M
LM
Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2.
Hultin
Philip G
PG
D000577:Amides / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000577:Amides; D001572:Benzofurans; D004987:Ethers; D006843:Hydrocarbons, Chlorinated; D014753:Vinyl Compounds