Pd-Catalyzed coupling of benzyl bromides with BMIDA-substituted N-tosylhydrazones: synthesis of trans-alkenyl MIDA boronates

A palladium-catalyzed stereoselective synthesis of alkenyl boronates from N-methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides is developed. A range of trans-alkenyl MIDA boronates as single stereoisomers were obtained in moderate yields with good functional group compatibility. The resultant boronate products may be transformed to other boron-containing compounds and may also be directly used in cross-coupling reactions.

Automated summary

A palladium-catalyzed stereoselective synthesis method has been developed for obtaining trans-alkenyl MIDA boronates from N-Methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides. The products show moderate yields and good functional group compatibility, with potential applications in the synthesis of other boron-containing compounds or in cross-coupling reactions.