Arylation of rhodium(II) azavinyl carbenes with boronic acids.
A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Nicklas
N
Selander
Brady T
BT
Worrell
Stepan
S
Chuprakov
Subash
S
Velaparthi
Valery V
VV
Fokin
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D001372:Aza Compounds; D001897:Boronic Acids; D009942:Organometallic Compounds; C030011:carbene; D012238:Rhodium; D008697:Methane