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C-H addition reactivity of 2-phenylpyridine and 2,2'-bipyridine with pentaphenylborole.
The reactions of pentaphenylborole with pyridines with a pendent aryl group in the 2-position, specifically 2-phenylpyridine and 2,2'-bipyridine, readily afforded adducts. Upon thermolysis, the adducts converted to ortho C-H addition products with the two substituents introduced onto the diene on the boracyclic carbon atoms adjacent to boron in a syn fashion. Photolysis of the syn 2-phenypyridine product led to isomerization to the anti conformer which did not readily occur for the 2,2'-bipyridine complex. Such C-H bond reactivity is uncommon for main group elements and provides insight into methodologies to access boron frameworks.
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