Synthesis 2014; 46(17): 2312-2316
DOI: 10.1055/s-0033-1340192
paper
© Georg Thieme Verlag Stuttgart · New York

Potassium tert-Butoxide Mediated O-Arylation of N-Hydroxyphthalimide and Oximes with Diaryliodonium Salts

Luis C. Misal Castro
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   Fax: +81(6)68797396   Email: chatani@chem.eng.osaka-u.ac.jp
,
Naoto Chatani*
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   Fax: +81(6)68797396   Email: chatani@chem.eng.osaka-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 31 March 2014

Accepted after revision: 30 April 2014

Publication Date:
12 June 2014 (online)


Abstract

A metal-free method for the direct O-arylation of N-hydroxyphthalimide­, pyridine-2-carboxaldehyde oxime, acetophenone oxime, or dimethylglyoxime with diaryliodonium salts under mild reaction conditions and short reaction time in the presence of potassium tert-butoxide is reported. The diaryliodonium counterion salt plays an important role in the reaction when it is carried out at 40 °C or lower temperatures.

Supporting Information