Progress in the Syntheses of α-Boryl Carbonyl Compounds

alpha-Boryl carbonyl compounds have traditionally been considered thermodynamically unstable and prone to undergo 1,3-boron migration. In recent years, with the development and understanding of sp(3)-hybridized boron or tetra-coordinated boron, methods for synthesizing stable and separable alpha-boryl carbonyl compounds have been actively developed. These methods include the insertion reaction of borane with diazo esters, sulfur ylides and other carbene precursors, the free-radical borylation reaction of alpha,beta-unsaturated carbonyl compounds, and late-stage structural modification reactions of boron-containing compounds. The recent advances in the synthesis of alpha-boryl carbonyl compounds are reviewed based on different reaction types, and the existing challenges and future research directions are discussed.

Automated summary

Alpha-boryl carbonyl compounds have traditionally been considered thermodynamically unstable and prone to undergo 1,3-boron migration. In recent years, methods for synthesizing stable and separable alpha-boryl carbonyl compounds have been actively developed, thanks to the development and understanding of sp(3)-hybridized boron or tetra-coordinated boron. These methods include the insertion reaction of borane with diazo esters, sulfur ylides and other carbene precursors, the free-radical borylation reaction of alpha,beta-unsaturated carbonyl compounds, and late-stage structural modification reactions of boron-containing compounds. The recent advances in the synthesis of alpha-boryl carbonyl compounds are reviewed based on different reaction types, and the existing challenges and future research directions are discussed.