(Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications

Area of Science:

• Organoboron Chemistry
• Synthetic Organic Chemistry
• Catalysis

Background:

• (Poly)borylated species are crucial building blocks in synthetic chemistry due to their tunable reactivity.
• Their unique steric and electronic properties enable participation in ionic and radical pathways for selective bond formation.
• These compounds are valuable for late-stage functionalization and constructing complex molecular architectures.

Purpose of the Study:

• To review recent advancements in the chemistry of (poly)borylated compounds, especially those with multiple boron substituents on a single carbon.
• To emphasize anionic, cationic, radical, alkene, 1,2-diradical, and carbene variants.
• To elucidate mechanistic principles and synthetic potential for understanding reactivity and applications.

Main Methods:

• Review of literature focusing on advances since 2019.
• Analysis of reactivity modes across various structural classes (gem-diborylalkanes, gem-diborylalkenes, etc.).
• Discussion of key transformations: cross-couplings, transmetalations, additions, polymerizations, and radical/photocatalysis reactions.

Main Results:

• Highlights synergistic behavior of multiple boron-substituted intermediates.
• Examines diverse functionalization of carbon-metalloid bonds.
• Covers boron-masking, boron-retentive, and boron-eliminative strategies.

Conclusions:

• Significant advances have been made in understanding the reactivity and synthetic utility of (poly)borylated species.
• These compounds offer strategic opportunities at the interface of organoboron chemistry, catalysis, and materials science.
• The review provides a unified framework for their application in modern synthesis.