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Microwave‐Assisted Radical Insertion/Cyclization of Vinyl Isocyanides for the Synthesis of Multi‐Substituted Isoquinolines
Author(s) -
Xu Yulong,
Chen Hao,
Li Wei,
Xie Qiong,
Yu Linqian,
Shao Liming
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701896
Subject(s) - heteroatom , radical cyclization , chemistry , radical , photochemistry , kinetic isotope effect , free radical reaction , substrate (aquarium) , microwave , combinatorial chemistry , medicinal chemistry , organic chemistry , ring (chemistry) , computer science , physics , oceanography , deuterium , quantum mechanics , geology , telecommunications
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.