Issue 4, 2016

Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone

Abstract

A K2S2O8-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency. The prepared 3-bromocoumarins are successfully converted into 3-alkynyl and 3-phosphite coumarins under mild conditions. The synthesis of a specific bromo-incorporated spiro-[4,5]trienyl-2,8-dione is achieved under the same conditions when N-methyl-N,3-diphenylpropiolate is used as the substrate.

Graphical abstract: Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone

Supplementary files

Article information

Article type
Research Article
Submitted
23 ene. 2016
Accepted
17 feb. 2016
First published
18 feb. 2016

Org. Chem. Front., 2016,3, 510-515

Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone

G. Qiu, T. Liu and Q. Ding, Org. Chem. Front., 2016, 3, 510 DOI: 10.1039/C6QO00041J

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