This work was financially supported by MIUR-FIRB (CINECA RBF12083M5N), the University of Bari, and Interuniversities Consortium C.I.N.M.P.I.S. We would like to acknowledge Dr. Francesca Sassone for her contribution to the Experimental Section.
Exploiting the Lithiation-Directing Ability of Oxetane for the Regioselective Preparation of Functionalized 2-Aryloxetane Scaffolds under Mild Conditions†
Article first published online: 13 JUN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 30, pages 7532–7536, July 23, 2012
How to Cite
Coppi, D. I., Salomone, A., Perna, F. M. and Capriati, V. (2012), Exploiting the Lithiation-Directing Ability of Oxetane for the Regioselective Preparation of Functionalized 2-Aryloxetane Scaffolds under Mild Conditions . Angew. Chem. Int. Ed., 51: 7532–7536. doi: 10.1002/anie.201109113
- Issue published online: 18 JUL 2012
- Article first published online: 13 JUN 2012
- Manuscript Revised: 15 MAR 2012
- Manuscript Received: 23 DEC 2011
- MIUR-FIRB. Grant Number: CINECA RBF12083M5N
- isotope effects;
Oxetane nudges in the DoM direction! Regioselective ortho-lithiation induced by an oxetane ring has been achieved. The reaction provides easy access to ortho-functionalized 2-aryloxetanes also through a lithiation/borylation Suzuki–Miyaura cross-coupling. The lithiation-directing ability of oxetane and the proton transfer mechanism have been investigated by competitive metalation and kinetic isotope effect studies.