Issue 66, 2012
From the journal:

Chemical Communications

Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenesvia a homolytic aromatic substitution mechanism†

Louis-Philippe B. Beaulieu,a   Daniela Sustac Roman,a   Frédéric Valléea  and  André B. Charette*a  

* Corresponding authors

a FRQNT Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Québec, Canada
E-mail: andre.charette@umontreal.ca
Fax: 01 514 343 7586
Tel: 01 514 343 6283

Abstract

A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)4 and NaHMDS. Mechanistic investigations support the catalytic nature of Ni0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.

Graphical abstract: Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

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Article information

DOI
https://doi.org/10.1039/C2CC33547F
Article type
Communication
Submitted
16 May 2012
Accepted
29 Jun 2012
First published
29 Jun 2012

Chem. Commun., 2012,48, 8249-8251

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Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

L. B. Beaulieu, D. S. Roman, F. Vallée and A. B. Charette, Chem. Commun., 2012, 48, 8249 DOI: 10.1039/C2CC33547F

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