Journal of Organic Chemistry p. 8341 - 8353 (2015)
Update date:2022-08-15
Topics:
Kallepalli, Venkata A
Gore, Kristin A.
Shi, Feng
Sanchez, Luis
Chotana, Ghayoor A.
Miller, Susanne L.
Maleczka, Robert E.
Smith, Milton R.
Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as clopidogrel.
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