Issue 1, 2001

Palladium-catalysed annulation of β-chloro-α,β-unsaturated esters with internal alkynes leading to 2H-pyran-2-ones

Abstract

Heteroannulation of β-chloro-α,β-unsaturated esters with internal alkynes proceeded in the presence of triethylamine and palladium complexes, bis(triphenylphosphine)palladium species in particular, to afford to 2H-pyran-2-ones. Treatment of methyl (Z)-3-chloro-2-heptenoate with Pd(PPh3)4 generates [(Z)-1-butyl-2-methoxycarbonylethenyl]chlorobis(triphenylphosphine)palladium [italic v (to differentiate from Times ital nu)]ia oxidative addition, which gives the corresponding 2H-pyran-2-one upon addition of 4-octyne. Terminal alkynes also reacted with β-chloro-α,β-unsaturated esters, but the major products were β-alkynylated α,β-unsaturated esters.

Article information

Article type
Paper
Submitted
15 Sep 2000
Accepted
06 Oct 2000
First published
05 Dec 2000

New J. Chem., 2001,25, 179-184

Palladium-catalysed annulation of β-chloro-α,β-unsaturated esters with internal alkynes leading to 2H-pyran-2-ones

R. Hua and M. Tanaka, New J. Chem., 2001, 25, 179 DOI: 10.1039/B007620L

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements