Year: 2024
Type: article
Abstract: A simplified one-pot procedure for the synthesis of a useful class of mixed chloro-/fluoroaryl boranes following the formula B(C 6 Cl 5 ) n (C 6 F 5 ) 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(C 6 Cl 5 )(C 6 F 5 ) 2 being the most active of the boranes studied. This mono-C 6 Cl 5 borane was able to cleave or reduce the C–O bond of ethers, carbonyls, and sugars under benchtop (open air) conditions. B(C 6 Cl 5 )(C 6 F 5 ) 2 thus demonstrates a favorable balance of water tolerance and preserved reactivity relative to that of BCF itself.
Source: Organometallics
Authors: Nathan E. DeSousa, Michel R. Gagné
Institution: University of North Carolina at Chapel Hill
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4404544859