Synthesis of methylene-bridged α,β-unsaturated ketones: α-C-H methylenation of aromatic ketones using Selectfluor as a mild oxidant

A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The reaction employs tetramethylethylenediamine (TMEDA) as a methylene and terminal olefin source, and Selectfluor as a mild oxidant. TMEDA worked...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 2; pp. 415 - 419
Main Authors Zhang, Yuan, Liu, Zhiqi, Zhu, Tingyu, Huang, Ying, Fan, Weibin, Huang, Deguang
Format Journal Article
Published 05.01.2022
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Summary:A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The reaction employs tetramethylethylenediamine (TMEDA) as a methylene and terminal olefin source, and Selectfluor as a mild oxidant. TMEDA worked as a dual synthon to provide two carbons in this metal-free transformation process. The scope and versatility of the methods have been demonstrated with 23 examples. A Selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies. A three starting material four component reaction is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones. TMEDA is used a dual synthon to provide two carbons in the Selectfluor system.
Bibliography:1
H NMR and
For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available: Experimental procedure and characterization data; crystallographic data
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C NMR spectra of products. CCDC
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2112455
10.1039/d1ob02043a
2112454
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02043a