Financial support for this work is acknowledged (grant nos. CTQ2007-61048 and IB08-088). S.S.-P. and D.P. thank the MICINN for predoctoral FPU fellowships. We also thank Dr. Ángel L. Suárez-Sobrino for his helpful assistance with the X-ray analysis. We are grateful to the referees for their kind and helpful suggestions to improve the manuscript, particularly for the labeling experiments.
Consecutive CH Functionalization Reactions of Arenes: Synthesis of Carbo- and Heteropolycyclic Skeletons†
Article first published online: 11 SEP 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 42, pages 7857–7861, October 5, 2009
How to Cite
Suárez-Pantiga, S., Palomas, D., Rubio, E. and González, José M. (2009), Consecutive CH Functionalization Reactions of Arenes: Synthesis of Carbo- and Heteropolycyclic Skeletons. Angew. Chem. Int. Ed., 48: 7857–7861. doi: 10.1002/anie.200902989
- Issue published online: 30 SEP 2009
- Article first published online: 11 SEP 2009
- Manuscript Revised: 7 AUG 2009
- Manuscript Received: 3 JUN 2009
- Lewis acids;
- propargylic esters
Doubling the bet: Two CH bonds become functionalized upon exposure of ω-aryl propargylic tosylates to Sc(OTf)3 (see scheme). The reaction involves a new domino process that can tolerate both electron-withdrawing and -donating substituents on the arene unit. Different carbo- and heterocyclic frameworks can be assembled by using this approach to formally conquer the hydroarylation process.