Palladium-Catalyzed Catellani Reaction with 1,1-Bis[(pinacolato)boryl]methane as the Nucleophilic Component

We report herein the application of 1,1-bis[(pinacolato)boryl]methane as a new type of terminating reagent to realize three-component coupling reaction with aryl iodide and different electrophiles. A series of ortho-disubstituted benzylboronates can be synthesized and the ortho-substituent can be varied by using bromoacetic esters or O-benzoyl hydroxylamine as electrophiles with slightly modified reaction conditions. The reaction shows good functional group tolerance and the obtained benzyl boronate products can be easily transformed to various synthetically useful compounds.

Automated summary

We report the use of 1,1-bis[(pinacolato)boryl]methane as a new terminating reagent for a three-component coupling reaction involving aryl iodide and various electrophiles. By using bromoacetic esters or O-benzoyl hydroxylamine as electrophiles with slightly modified reaction conditions, a series of ortho-disubstituted benzylboronates can be synthesized, allowing for variation in the ortho-substituent. The reaction exhibits good tolerance towards different functional groups, and the resulting benzyl boronate products can be easily converted into diverse synthetically useful compounds.