Issue 18, 2000
From the journal:

Chemical Communications

Palladium catalyzed intramolecular nucleophilic addition of allylic species, generated from allene, to aryl aldehydes and ketones

Xinjie Gai,a   Ronald Grigg,*a   Simon Collardb  and  Jayne E. Muirb  

* Corresponding authors

a Molecular Innovation, Diversity and Automated Synthesis (MIDAS) Centre, School of Chemistry, Leeds University, Leeds, UK
E-mail: R.Grigg@chem.leeds.ac.uk

b Johnson Matthey, Precious Metal Division, Hertfordshire, Royston, UK

Abstract

2-Haloaryl aldehydes and ketones react with allene (1 atm) in the presence of 2 mol% of a non-phosphine cyclopalladated catalyst to afford cyclopentenols and cyclohexenols via nucleophilic cyclisation of intermediate π-allylpalladium species. A possible mechanism for this unusual reactivity is suggested.

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Article information

DOI
https://doi.org/10.1039/B005740L
Article type
Communication
Submitted
17 Jul 2000
Accepted
27 Jul 2000
First published
29 Aug 2000

Chem. Commun., 2000, 1765-1766

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Palladium catalyzed intramolecular nucleophilic addition of allylic species, generated from allene, to aryl aldehydes and ketones

X. Gai, R. Grigg, S. Collard and J. E. Muir, Chem. Commun., 2000, 1765 DOI: 10.1039/B005740L

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