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Intramolecular Aminocyanation of Alkenes by NCN Bond Cleavage
Author(s) -
Pan Zhongda,
Pound Sarah M.,
Rondla Naveen R.,
Douglas Christopher J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310983
Subject(s) - intramolecular force , cleavage (geology) , chemistry , bond cleavage , medicinal chemistry , stereochemistry , materials science , organic chemistry , catalysis , composite material , fracture (geology)
A metal‐free, Lewis acid promoted intramolecular aminocyanation of alkenes was developed. B(C 6 F 5 ) 3 activates N‐sulfonyl cyanamides, thus leading to a formal cleavage of the NCN 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.