Intramolecular Aminoboration of Unfunctionalized Olefins.
A direct and catalyst-free method for the intramolecular aminoboration of unfunctionalized olefins is reported. In the presence of BCl3 (1 equiv) as the sole boron source, intramolecular aminoboration of sulfonamide derivatives of 4-penten-1-amines, 5-hexen-1-amines, and 2-allylanilines proceeded readily without the use of any catalyst. The boronic acids obtained after hydrolysis could be converted into the corresponding pinacol borates in a straightforward manner by treatment with pinacol under anhydrous conditions.
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China).
Chun-Hua
CH
Yang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China).
Yu-Shi
YS
Zhang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China).
Wen-Wen
WW
Fan
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China).
Gong-Qing
GQ
Liu
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China). ymli@nankai.edu.cn.|CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China). ymli@nankai.edu.cn.
Yue-Ming
YM
Li
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006868:Hydrolysis
D000475:Alkenes; D000588:Amines; D001897:Boronic Acids; D001895:Boron
Suzuki cross-coupling; aminoboration; boronic acids; boronic esters; synthetic methods