Mixed Chloro-/Fluoroaryl Boranes as Lewis Acid Catalysts for C–O Bond Cleavage/Reduction

IF 2.5 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR

Organometallics Pub Date : 2024-11-20 DOI:10.1021/acs.organomet.4c0042010.1021/acs.organomet.4c00420

Nathan E. DeSousa, and , Michel R. Gagné*,

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Abstract

A simplified one-pot procedure for the synthesis of a useful class of mixed chloro-/fluoroaryl boranes following the formula B(C₆Cl₅)_n(C₆F₅)_3–n is reported. Standard organolithium and Grignard reagents are utilized, and intermediate arylzinc or arylcopper reagents are not required. With regard to their applications to C–O cleavage reactions, the increased steric bulk of having ortho-chlorine enhances the catalyst tolerance of water, allowing for C–O deoxygenations under atmospheric conditions. As the degree of chlorination increases, the reactivity of the borane catalyst decreases with B(C₆Cl₅)(C₆F₅)₂ being the most active of the boranes studied. This mono-C₆Cl₅ borane was able to cleave or reduce the C–O bond of ethers, carbonyls, and sugars under benchtop (open air) conditions. B(C₆Cl₅)(C₆F₅)₂ thus demonstrates a favorable balance of water tolerance and preserved reactivity relative to that of BCF itself.

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来源期刊

Organometallics 化学-无机化学与核化学

CiteScore

5.60

自引率

7.10%

发文量

382

审稿时长

1.7 months

期刊介绍： Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.