Regiocontrolled Cleavage of Dialkyl Ethers Using Regenerative Borates as a Sustainable Alternative to Boron Trichloride

Theodora E. Leventis; Noah G. Veatch; Florence J. Williams

doi:10.1002/ejoc.202500649

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Regiocontrolled Cleavage of Dialkyl Ethers Using Regenerative Borates as a Sustainable Alternative to Boron Trichloride

Journal article

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Regiocontrolled Cleavage of Dialkyl Ethers Using Regenerative Borates as a Sustainable Alternative to Boron Trichloride

Theodora E. Leventis, Noah G. Veatch and Florence J. Williams

European journal of organic chemistry, Vol.28(40), e202500649

10/29/2025

DOI: 10.1002/ejoc.202500649

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Abstract

Ethers are ubiquitous functional groups in natural products, surfactants, and materials, making them valuable targets for chemical diversification. This report advances a previously reported method utilizing a 1:1 mixture of BBr 3 and BCl 3 to cleave unsymmetric dialkyl ethers with high regio‐ and chemoselectivity. In this new protocol, regenerable triaryl borates are used in place of BCl 3 , offering a more sustainable approach. Importantly, all boron‐containing byproducts from the reaction can be converted back into the triaryl borate, enabling full reagent recovery. The speciation of borate/BBr 3 mixtures is monitored by 11 B‐NMR and compared to the previously studied BCl 3 /BBr 3 system. Additionally, Design of Experiments (DOE) statistical analysis reveals a correlation between borate Lewis acidity and cleavage selectivity. The triaryl borate regenerated in situ from aqueous waste performs comparably to freshly prepared material in subsequent reactions. Overall, this system matches or exceeds the performance of the original BBr 3 /BCl 3 method across a broad range of dialkyl ether substrates.

borate regeneration

boron Lewis acids

boron recyclability

dialkyl ether cleavage

regioselectivity

UIOWA OA Agreement

Details

Title: Subtitle: Regiocontrolled Cleavage of Dialkyl Ethers Using Regenerative Borates as a Sustainable Alternative to Boron Trichloride
Creators: Theodora E. Leventis - University of Iowa
Noah G. Veatch - University of Iowa
Florence J. Williams - University of Iowa
Resource Type: Journal article
Publication Details: European journal of organic chemistry, Vol.28(40), e202500649
DOI: 10.1002/ejoc.202500649
ISSN: 1434-193X
eISSN: 1099-0690
Publisher: Wiley
Grant note: Herman Frasch Foundation for Chemical Research
This work was supported by the National Science Foundation (CAREER Award CHE 2239556) and the Herman Frasch Foundation for Chemical Research in Agricultural Chemistry, K4525.
Language: English
Electronic publication date: 08/28/2025
Date published: 10/29/2025
Academic Unit: Iowa Neuroscience Institute; Chemistry
Record Identifier: 9984958291902771

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