Categories: C-H Bond Formation >
A mild gold-catalyzed protodeboronation reaction can be carried out in green solvents without any acid or base additives. Therefore, the reaction is very functional-group-tolerant and enables the use of the boronic acid group as an effective traceless directing or blocking group.
G. Barker, S. Webster, D. G. Johnson, R. Curley, M. Andrews, P. C. Young, S. A. Macgregor, A.-L. Lee, J. Org. Chem., 2015, 80, 9807-9816.
CsF with 1.1 equiv of H2O effects highly efficient protodeboronation on tertiary diarylalkyl boronic esters with essentially complete retention of configuration, whereas TBAFˇ3H2O can be used for tertiary aryldialkyl boronic esters. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. A short synthesis of the sesquiterpene (S)-turmerone is described.
S. Nave, R. P. Sonawane, T. G. Elford, V. K. Aggarwal, J. Am. Chem. Soc., 2010, 132, 17096-17098.