Defluorinative Diborasodiation of Benzotrifluorides with Bis(pinacolato)Diboron and Sodium

Treatment of benzotrifluorides with sodium dispersion in the presence of bis(pinacolato)diboron results in diborative reduction to yield the corresponding diborylbenzylsodium species. The anionic species react not only with reactive organic halides but also with aromatic carbonyl compounds to yield the corresponding alkenylboron compounds via Peterson-type olefination. The success of the generation of the diborylbenzylsodium species lies in immediate capture of initially formed unstable difluorobenzylsodium with co-existing reduction-resistant bis(pinacolato)diboron.

Automated summary

Treatment of benzotrifluorides with sodium dispersion in the presence of bis(pinacolato)diboron leads to diborative reduction to obtain diborylbenzylsodium species. These anionic species not only react with reactive organic halides, but also with aromatic carbonyl compounds to produce alkenylboron compounds via Peterson-type olefination. The key to the success of generating diborylbenzylsodium species lies in the immediate capture of unstable difluorobenzylsodium with co-existing reduction-resistant bis(pinacolato)diboron.