Electrochemical deconstruction of alkyl substituted boron clusters to produce alkyl boronate esters

Closo-Hexaborate (closo-B6H62-) can engage in nucleophilic substitution reactions with a wide variety of alkyl electrophiles. The resulting functionalized boron clusters undergo oxidative electrochemical deconstruction, selectively cleaving B-B bonds while preserving B-C bonds in these species. This approach allows the conversion of multinuclear boron clusters into single boron site organoboranes. Trapped boron-based fragments were isolated from the electrochemical cluster deconstruction process, providing further mechanistic insights into the developed reaction. In situ generated hexaborate dianions can engage in nucleophilic substitution followed by bulk electrolysis to produce organoboronate esters.