Palladium(II)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction.
A mild and novel palladium(II)-catalyzed domino Heck/Suzuki alpha,beta-diarylation-reduction of a dimethylaminoethyl substituted chelating vinyl ether was developed by using electron-rich arylboronic acids in combination with p-benzoquinone. Based on the preparative results, a catalytic cycle is proposed. Further, highly regioselective palladium(II)-catalyzed alpha- or beta-monoarylation of the chelating vinyl ether was achieved using either a bidentate ligand or by employing ligand-less conditions.
Trejos
Alejandro
A
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden.
Fardost
Ashkan
A
Yahiaoui
Samir
S
Larhed
Mats
M
D016227:Benzoquinones / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D016227:Benzoquinones; D001897:Boronic Acids; D002614:Chelating Agents; D004987:Ethers; D014753:Vinyl Compounds; C100195:vinyl ether; C004532:quinone; D010165:Palladium