Issue 11, 2012
From the journal:

Organic & Biomolecular Chemistry

Scope of direct arylation of fluorinated aromatics with aryl sulfonates†

Joyce Wei Wei Chang,a   Eugene Yurong Chia,a   Christina Li Lin Chaiab  and  Jayasree Seayad*a  

* Corresponding authors

a Institute of Chemical and Engineering Sciences, 8 Biomedical Grove, Neuros, #07-01, Singapore 138665, Singapore
E-mail: jayasree_seayad@ices.a-star.edu.sg
Fax: +(65) 6464 2102
Tel: +(65) 6799 8515

b Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore

Abstract

The scope and limitations of direct arylation of fluorinated aromatics with aryl sulfonates was examined. Pd(OAc)2, in the presence of MePhos and KOAc in THF, efficiently catalyzed the direct arylation of fluoro aromatics with aryl triflates under ambient conditions. Sterically hindered triflates and heteroaryl triflates gave good to excellent yields of the cross coupled products using a modified catalyst system which involves Pd(OAc)2–RuPhos at 100 °C. The direct arylation of electron deficient arenes with aryl mesylates is also established using Pd(OAc)2–SPhos as the catalyst in toluene–tBuOH at 120 °C.

Graphical abstract: Scope of direct arylation of fluorinated aromatics with aryl sulfonates

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Article information

DOI
https://doi.org/10.1039/C2OB06840K
Article type
Paper
Submitted
02 Nov 2011
Accepted
16 Jan 2012
First published
17 Jan 2012

Org. Biomol. Chem., 2012,10, 2289-2299

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Scope of direct arylation of fluorinated aromatics with aryl sulfonates

J. W. W. Chang, E. Y. Chia, C. L. L. Chai and J. Seayad, Org. Biomol. Chem., 2012, 10, 2289 DOI: 10.1039/C2OB06840K

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