Intramolecular Aminocyanation of Alkenes by N-CN Bond Cleavage

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2014 Apr 11

PMID 24719371

Citations 8

Authors

Zhongda Pan

Sarah M Pound

Naveen R Rondla

Christopher J Douglas

Affiliations

Soon will be listed here.

Abstract

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.

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