Fe-Catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to construct 3,4-dihydroquinolin-2(1H)-ones?
Organic & Biomolecular Chemistry Pub Date: 2019-05-02 DOI: 10.1039/C9OB00492K
Abstract
A practical Fe-catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to provide C3 alkylated 3,4-dihydroquinolin-2(1H)-ones is developed. Aliphatic aldehydes were oxidatively decarbonylated into 1°, 2° and 3° alkyl radicals conveniently, allowing for the subsequent cascade construction of C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds via radical addition and HAS-type cyclization. The importance of the amide linkage and the selectivity of the 6-endo-trig over 5-exo-trig cyclization pathway were elucidated by experimental results and DFT calculations.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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