Synthesis of methylene-bridged α,β-unsaturated ketones: α-C sp 3 -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...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 20; no. 2; pp. 415 - 419
Main Authors Zhang, Yuan, Liu, Zhiqi, Zhu, Tingyu, Huang, Ying, Fan, Weibin, Huang, Deguang
Format Journal Article
LanguageEnglish
Published England 05.01.2022
Online AccessGet full text

Cover

More Information
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.
ISSN:1477-0520
1477-0539
DOI:10.1039/D1OB02043A