Metalations utilizing aryllithiums; ortho-functionalization of p-bromoanisole (pBrA)

DW Slocum, TL Reece, RD Sandlin, TK Reinscheld…

Index: Slocum; Reece, Troy L.; Sandlin, Rebecca D.; Reinscheld, Thomas K.; Whitley, Paul E. Tetrahedron Letters, 2009 , vol. 50, # 14 p. 1593 - 1595

Full Text: HTML

Citation Number: 6

Abstract

An ortho-metalation protocol has been developed, which permits the survival of a bromine substituent in p-bromoanisole. Eight derivatives of the generated ortho-lithiated intermediate have been prepared. A neglected metalation concept is being explored here; one which proposes that minimizing the pKa difference between the aryl substrate and the conjugate acid of the metalating agent will lead to a regiospecific and selective metalation process.