Aminochlorination in water: first Brønsted acid-promoted synthesis of vicinal chloramines.
A practical and scaleable route for the regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T promoted by Brønsted acids in water has been realized for the first time. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including alpha,beta-unsaturated ketones, cinnamate, and cinnamide. Water represents as a privileged solvent for the aminochlorination reaction in our system.
Wu
Xue-Liang
XL
Hefei National Laboratory for Physical Sciences at Microscale, Joint Laboratory of Green Synthetic Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, PR China.
Wang
Guan-Wu
GW
D000143:Acids / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D000586:Amination; D002700:Chloramines / Q000138:chemical synthesis*; D002712:Chlorides / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000143:Acids; D000577:Amides; D002700:Chloramines; D002712:Chlorides; D002934:Cinnamates; D007659:Ketones; D012997:Solvents; D014867:Water