Atroposelective Suzuki-Miyaura Coupling Reaction with Benzoxaboroles

Area of Science:

• Organic Chemistry
• Asymmetric Catalysis
• Organoboron Chemistry

Background:

• Suzuki-Miyaura cross-coupling is a vital tool for C-C bond formation.
• Axial chirality is crucial in pharmaceuticals and materials science.
• Benzoxaboroles are versatile building blocks with untapped potential in asymmetric synthesis.

Purpose of the Study:

• To develop a novel asymmetric ring-opening Suzuki-Miyaura cross-coupling (SMC) reaction.
• To enable the synthesis of diverse axial chiral biaryl benzyl alcohols.
• To explore the utility of cyclic benzoxaboroles in asymmetric transformations.

Main Methods:

• Utilized ortho-disubstituted aryl bromides and cyclic benzoxaboroles.
• Employed a commercially available chiral phosphine ligand (Et-AntPhos).
• Optimized reaction conditions for high enantioselectivity.

Main Results:

• Achieved the first asymmetric ring-opening SMC reaction of cyclic benzoxaboroles.
• Generated diverse axial chiral biaryl benzyl alcohols with high enantioselectivity (up to 97:3 er).
• Demonstrated mild reaction conditions and a broad substrate scope.

Conclusions:

• The developed protocol provides general access to valuable axial chiral compounds.
• Cyclic benzoxaboroles are effective substrates for asymmetric Suzuki-Miyaura cross-coupling.
• This method expands the synthetic utility of benzoxaboroles in asymmetric catalysis.