Randomized trial demonstrates efficient synthesis of carborane-containing esters, suggesting a new method for organic reactions.
-carboxylated carboranes with α-allenols, enabling direct access to carborane-containing 1,3-dien-2-yl esters under mild conditions. This operationally simple protocol proceeds via dehydration of a protonated α-allenol to generate a putative α-allenyl carbocation, which is efficiently intercepted by the corresponding carboranyl carboxylate. The synthetic utility of the resulting dienyl esters is demonstrated through Diels-Alder reactions with representative dienophiles. Mechanistic investigations support the unique reactivity of carboranyl carboxylic acids and a pathway distinct from transition-metal-catalyzed intramolecular acyloxy migration manifolds.
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Kim et al. (2026) studied this question.
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