Journal article
Reductive Deoxygenation of Aromatic Aldehydes and Ketones with Boron Triiodide
Journal of organic chemistry
08/13/2026
DOI: 10.1021/acs.joc.6c01013
Abstract
Deoxygenation of carbonyls is an area of value in synthetic transformations because it allows for the traceless utilization of carbonyl chemistry, a mainstay in synthetic manipulations. Since oxygenation patterns are common in biological settings, deoxygenation can also be used to valorize biologically derived feedstocks. Herein, we describe the use of potassium borohydride and iodine, two common and benchtop-stable reagents, to generate boron triiodide in situ, which performs full deoxygenation of aryl aldehydes and ketones. For aldehydes, benzyl iodide products are formed, whereas for ketones, the fully reduced methylene is produced. Byproducts upon workup are low-toxicity boric acid and iodide salts, making the process practical and appealing for a wide range of applications.
Details
- Title: Subtitle
- Reductive Deoxygenation of Aromatic Aldehydes and Ketones with Boron Triiodide
- Creators
- Thomas M. Chiarella - University of IowaAnthony P. Furrule - University of IowaFlorence J. Williams - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry
- DOI
- 10.1021/acs.joc.6c01013
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Grant note
- Division of Chemistry: CHE 2239556
This study was funded by National Science Foundation Career Award CHE 2239556.
- Language
- English
- Electronic publication date
- 08/13/2026
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9985219867802771
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