Bis(cycloocta‐1,5‐diene)nickel‐Catalyzed Carbon Dioxide Fixation for the Stereoselective Synthesis of 3‐Alkylidene‐2‐indolinones

A bis(cycloocta‐1,5‐diene)nickel‐catalyzed highly regio‐ and (E)‐stereoselective hydrocarboxylation of 2‐alkynylanilines under very mild conditions has been developed to afford (E)‐[2‐(o‐aminophenyl)]acrylic acids, which could easily be converted to (E)‐3‐alkylidene‐2‐indolinones with important pote...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-05, Vol.359 (10), p.1691-1707
Main Authors: Miao, Bukeyan, Zheng, Yangguangyan, Wu, Penglin, Li, Suhua, Ma, Shengming
Format: Article
Language:English
Subjects:
2-alkylanilines
Acrylic acid
acrylic acids
Alkylidene
Biochemistry
Biocompatibility
Biomedical materials
bis(cycloocta-1,5-diene)nickel [Ni(COD)2]
Carbon dioxide
Chemical synthesis
Fixation
hydrocarboxylation
Nickel
Surgical implants
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Summary:A bis(cycloocta‐1,5‐diene)nickel‐catalyzed highly regio‐ and (E)‐stereoselective hydrocarboxylation of 2‐alkynylanilines under very mild conditions has been developed to afford (E)‐[2‐(o‐aminophenyl)]acrylic acids, which could easily be converted to (E)‐3‐alkylidene‐2‐indolinones with important potential bioactivity. The stereoselective syntheses of two biologically active molecules, (E)‐3‐benzylidene‐2‐indolinone (chemo‐preventive potential in inducing NQO1 activity) and (E)‐3‐(3‐methylbutylidene)‐2‐indolinone (a natural product isolated from Cimicifuga foetida with cytotoxic activity against HL‐60 cells) are presented as examples.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700086