Microwave‐Assisted Radical Insertion/Cyclization of Vinyl Isocyanides for the Synthesis of Multi‐Substituted Isoquinolines. Issue 26 (13th September 2017)

• Record Type: Journal Article
• Authors: Xu, Yulong; Chen, Hao; Li, Wei; Xie, Qiong; Yu, Linqian; Shao, Liming
• Is Part Of: ChemistrySelect. Volume 2:Issue 26(2017)
• Page Start: 8033
• Page End: 8038
• Publication Date: 2017-09-13
• Subjects: C(sp3)-H bond -- Isoquinolines -- Microwave-assisted -- Radical -- Vinyl isocyanides; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701896
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A convenient microwave‐assisted method for the synthesis of multi‐substituted isoquinolines from the radical insertion/cyclization reaction of vinyl isocyanides with a C(sp 3 )‐H bond adjacent to a heteroatom has been described. The methodology presented here achieves wide substrate scope and good to excellent yields. A radical mechanism is proposed, which is supported by kinetic isotope effect (KIE) studies, radical trapping studies and Hammett plot analysis. Abstract : A convenient microwave‐assisted method for the synthesis of multi‐substituted isoquinolines from the radical insertion/cyclization reaction of vinyl isocyanides with a C(sp 3 )‐H bond adjacent to a heteroatom has been described. A radical mechanism is proposed, which is supported by kinetic isotope effect (KIE) studies, radical trapping studies and Hammett plot analysis.