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.
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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
DOI: 10.1002/anie.201109113
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
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
- †
Publication History
- Issue published online: 18 JUL 2012
- Article first published online: 13 JUN 2012
- Manuscript Revised: 15 MAR 2012
- Manuscript Received: 23 DEC 2011
Funded by
- MIUR-FIRB. Grant Number: CINECA RBF12083M5N
Keywords:
- cross-coupling;
- isotope effects;
- ortho-lithiation;
- oxetanes;
- phthalans
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.