Synthesis of 2- and 2,7-Functionalized Pyrene Derivatives: An Application of Selective CH Borylation (pages 5022–5035)
Dr. Andrew G. Crawford, Prof. Dr. Zhiqiang Liu, Prof. Dr. Ibraheem A. I. Mkhalid, Dr. Marie-Hélène Thibault, Dr. Nicolle Schwarz, Dr. Gilles Alcaraz, Dr. Andreas Steffen, Dr. Jonathan C. Collings, Dr. Andrei S. Batsanov, Prof. Dr. Judith A. K. Howard and Prof. Dr. Todd B. Marder
Version of Record online: 13 MAR 2012 | DOI: 10.1002/chem.201103774
The point of catalytic CH borylation! Regioselective iridium-catalyzed borylation of pyrene takes place at the 2- and 2,7-positions. The resulting mono- and bisboronate esters can be readily converted into both nucleophilic and electrophilic cross-coupling partners and serve as useful precursors to a wide range of pyrene derivatives of significant photophysical and structural interest, which are otherwise difficult to prepare (see scheme).