Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans.
Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, PR China.
Shihua
S
Wang
Pinhua
P
Li
Lin
L
Yu
Lei
L
Wang
D000480:Alkynes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D001966:Bromine / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D010647:Phenyl Ethers / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000480:Alkynes; D001572:Benzofurans; D010636:Phenols; D010647:Phenyl Ethers; D014753:Vinyl Compounds; D010165:Palladium; C096130:phenyl vinyl ether; D001966:Bromine