Issue 5, 2014

Copper-catalyzed oxidative ipso-carboalkylation of activated alkynes with ethers leading to 3-etherified azaspiro[4.5]trienones

Abstract

Cu-catalyzed synthesis of 3-etherified azaspiro[4.5]trienones from N-arylpropiolamides and ethers is presented using TBHP oxidant. This is achieved through C(sp3)–H functionalization, ipso-carbocyclization and dearomatization, and this method represents a new example of alkyne oxidative 1,2-difunctionalization with an ipso-aromatic carbon and a C(sp3)–H bond by simultaneously forming two new carbon–carbon bonds.

Graphical abstract: Copper-catalyzed oxidative ipso-carboalkylation of activated alkynes with ethers leading to 3-etherified azaspiro[4.5]trienones

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jan 2014
Accepted
12 Mar 2014
First published
09 Apr 2014

Org. Chem. Front., 2014,1, 484-489

Copper-catalyzed oxidative ipso-carboalkylation of activated alkynes with ethers leading to 3-etherified azaspiro[4.5]trienones

W. Wei, R. Song, X. Ouyang, Y. Li, H. Li and J. Li, Org. Chem. Front., 2014, 1, 484 DOI: 10.1039/C4QO00006D

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