We thank the NSF (CHE-0910641) for support, Johnson-Matthey for a gift of iridium, and Allychem for a gift of B2pin2. We also thank the American Chemical Society Division of Organic Chemistry (sponsored by Boehringer Ingelheim) for fellowship support (D.W.R.).
Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation†
Article first published online: 11 DEC 2012
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 3, pages 933–937, January 14, 2013
How to Cite
Robbins, D. W. and Hartwig, J. F. (2013), Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation . Angew. Chem. Int. Ed., 52: 933–937. doi: 10.1002/anie.201208203
- Issue published online: 11 JAN 2013
- Article first published online: 11 DEC 2012
- Manuscript Received: 11 OCT 2012
- NSF. Grant Number: CHE-0910641
Complementary chemistry: A one-pot method for the site-selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir-catalyzed CH borylation, followed by Pd- or Ni-catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel–Crafts alkylation; meta-selective alkylation of a broad range of arenes with various electronic properties and functional groups occurs in good yield with high site selectivity.