Intramolecular aminocyanation of alkenes by N-CN bond cleavage.
A metal-free, Lewis acid promoted intramolecular aminocyanation of alkenes was developed. B(C6F5)3 activates N-sulfonyl cyanamides, thus leading to a formal cleavage of the N-CN bonds in conjunction with vicinal addition of sulfonamide and nitrile groups across an alkene. This method enables atom-economical access to indolines and tetrahydroquinolines in excellent yields, and provides a complementary strategy for regioselective alkene difunctionalizations with sulfonamide and nitrile groups. Labeling experiments with (13)C suggest a fully intramolecular cyclization pattern due to the lack of label scrambling in double crossover experiments. Catalysis with Lewis acid is realized and the reaction can be conducted under air.
Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA).
Zhongda
Z
Pan
Sarah M
SM
Pound
Naveen R
NR
Rondla
Christopher J
CJ
Douglas
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D006868:Hydrolysis
D000475:Alkenes; D000588:Amines; D003486:Cyanides
Lewis acids; alkenes; boron; heterocycles; reaction mechanisms