Intramolecular Aminocyanation of Alkenes by NCN Bond Cleavage1. (9th April 2014)

• Record Type: Journal Article
• Authors: Pan, Zhongda; Pound, Sarah M.; Rondla, Naveen R.; Douglas, Christopher J.
• Is Part Of: Angewandte Chemie. Volume 126:Number 20(2014)
• Page Start: 5270
• Page End: 5274
• Publication Date: 2014-04-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201310983
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 ¹³C 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.</p> </abstract>