Regioselective C–H alkylation and alkenylation at the C5 position of 2-amino-1,4-naphthoquinones with maleimides under Rh(iii) catalysis

Rhodium(iii) catalyzed regioselective C–H alkylation and alkenylation at the C5 position of 1,4-naphthoquinone with maleimides under acidic and basic conditions, respectively, is described. The alkylamino substituents at the C2 position enabled the reaction to proceed efficiently. The alkylation rea...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-07, Vol.6 (14), p.2441-2446
Main Authors: Prasanna Anjaneyulu Yakkala, Giri, Deepesh, Chaudhary, Bharatkumar, Auti, Prashant, Sharma, Satyasheel
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Crystallography
NMR
Nuclear magnetic resonance
Organic chemistry
Regioselectivity
Rhodium
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Summary:Rhodium(iii) catalyzed regioselective C–H alkylation and alkenylation at the C5 position of 1,4-naphthoquinone with maleimides under acidic and basic conditions, respectively, is described. The alkylamino substituents at the C2 position enabled the reaction to proceed efficiently. The alkylation reaction proceeds via a redox neutral Rh(iii) pathway, whereas the alkenylation reaction takes place through the typical redox Rh(iii) pathway to yield Rh(i) species.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo00538b