Metal‐Free Meerwein Carboarylation of Alkenes with Anilines: A Straightforward Approach to 3‐Benzyl‐3‐alkyloxindoles. Issue 17 (28th April 2014)

• Record Type: Journal Article
• Authors: Tang, Shi; Zhou, Dong; Wang, Ying‐Chun
• Is Part Of: European journal of organic chemistry. Issue 17(2014)
• Page Start: 3656
• Page End: 3661
• Publication Date: 2014-04-28
• Subjects: Nitrogen heterocycles -- Domino reactions -- Radical reactions -- Cyclization -- Amines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402010
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A metal‐free, straightforward carboarylation reaction of alkenes with anilines was developed that proceeds through a radical C–H cyclization. In the presence of benzoyl peroxide (5 mol‐%), tert ‐butyl nitrite, and an array of anilines, a wide variety of N ‐arylacrylamides underwent a tandem Meerwein arylation/C–H cyclization to construct the pharmaceutically important 3‐benzyl‐3‐alkyloxindole scaffold in moderate to good yields. Abstract : A metal‐free, straightforward carboarylation reaction of alkenes with anilines was developed. In the presence of benzoyl peroxide, tert ‐butyl nitrite, and an array of anilines, a wide variety of N ‐arylacrylamides underwent a tandem Meerwein arylation/C–H cyclization to construct the pharmaceutically important 3‐benzyl‐3‐alkyloxindole scaffold in moderate to good yields.