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Regiodivergent Functionalization of Isoquinoline‐1,3(2 H ,4 H )‐dione Derivatives via Aerobic Umpolung
Author(s) -
Li YingXian,
Feng XiaoBing,
Jia XueMin,
Jin Huang,
Chen Fei,
Zhao YongLong,
Zhang JiQuan,
Wang JianTa,
Guo Bing,
Tang Lei,
Yang YuanYong
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100194
Subject(s) - chemistry , umpolung , isoquinoline , nucleophile , aldol reaction , surface modification , organocatalysis , heteroatom , divergent synthesis , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , stereochemistry , ring (chemistry)
A mild and green methodology for the regiodivergent functionalization of isoquinoline‐1,3(2 H ,4 H )‐diones under aerobic conditions was developed. Under a catalytic amount of base, heteroatom nucleophiles went through an imide opening/ring contraction sequence to give the thermodynamic controlled product; while carbon based nucleophiles led to kinetic controlled aldol type product. Moreover, the aldol type product was transformed into the benzo[c]phenanthridine core structures under transition metal free condition, which provides an environmental benign access to this framework.