Journal article
Reliably Regioselective Dialkyl Ether Cleavage with Mixed Boron Trihalides
Organic letters, Vol.20(20), pp.6332-6335
10/19/2018
DOI: 10.1021/acs.orglett.8b02356
PMID: 30265548
Abstract
A protocol for the regioselective cleavage of unsymmetrical alkyl ethers to generate alkyl alcohol and alkyl bromide products is described. A mixture of trihaloboranes triggers this conversion and exhibits improved reactivity profiles (regioselectivity and yield) compared with BBr
alone. Additionally, this procedure allows the efficient synthesis of (B-Cl) dialkyl boronate esters. There are limited methods to generate acyclic dialkoxyboryl chlorides, and these intermediates constitute important synthons in main-group chemistry.
Details
- Title: Subtitle
- Reliably Regioselective Dialkyl Ether Cleavage with Mixed Boron Trihalides
- Creators
- Bren Jordan P Atienza - Department of Chemistry , University of Alberta , Edmonton , AB , Canada T6G 2G2Nam Truong - Department of Chemistry , University of Alberta , Edmonton , AB , Canada T6G 2G2Florence J Williams - Department of Chemistry , University of Alberta , Edmonton , AB , Canada T6G 2G2
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.20(20), pp.6332-6335
- Publisher
- United States
- DOI
- 10.1021/acs.orglett.8b02356
- PMID
- 30265548
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- DOI: 10.13039/100006770, name: American Chemical Society Petroleum Research Fund, award: 59191-ND-1; DOI: 10.13039/501100000038, name: Natural Sciences and Engineering Research Council of Canada, award: RGPIN-2016-04843
- Language
- English
- Date published
- 10/19/2018
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984065470602771
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