Outer-Sphere Direction in Iridium C–H Borylation
Journal of the American Chemical Society2012Vol. 134(28), pp. 11350–11353
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Philipp C. Roosen, Venkata A. Kallepalli, Buddhadeb Chattopadhyay, Daniel A. Singleton, Robert E. Maleczka, Milton R. Smith
Abstract
The NHBoc group affords ortho selective C-H borylations in arenes and alkenes. Experimental and computational studies support an outer sphere mechanism where the N-H proton hydrogen bonds to a boryl ligand oxygen. The regioselectivities are unique and complement those of directed ortho metalations.
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