Achieving tunable site-selectivity in the functionalization of C–H bonds remains a desirable yet challenging objective in organic synthesis. This talk details two distinct approaches toward this objective. In the first approach, we employ electrochemistry to achieve the C–H carboxylation of pyridines. It was found that by changing the reaction vessel from a divided to undivided cell, the regioselectivity of the carboxylation reaction is completely reversed, a phenomenon that we attribute to a Curtin-Hammett control via paired electrolysis. In a second approach, we employ a new concept named Frustrated Radical Pairs to achieve the site-selective oxidation of C–H bonds. The selectivity is achieved through reagent-controlled hydrogen atom transfer.

New strategies for site-selective and tunable C–H functionalization

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