Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes and arenes. This involves: (1) regioselective Ar-H alkylation to form benzhydrylphosphonium salts via a one-pot, four-component reaction with simple reagents and (2) chemoselective reductions or oxidations of the benzylic C-P bond. Notably, reductions with D<sub>2</sub>O yield fully deuterated diarylmethanes. This high-yielding, straightforward approach offers valuable building blocks and enables novel transformations for academic and pharmaceutical research.

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Publication Details

Journal
Organic Letters
Published
2025-03-28
DOI
https://doi.org/10.1021/acs.orglett.5c00748
Citations
2
Primary Topic
Chemical Reactions and Isotopes
Type
article
Field-Weighted Citation Impact
1.58

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article

Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

Ahmad Masarwa, Nadim Eghbarieh, Israa Shioukhi, Nicole Hanania et al.
2 citations
Organic Letters
Chemical Reactions and Isotopes
1.58
article

Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

Ahmad Masarwa, Nadim Eghbarieh, Israa Shioukhi, Nicole Hanania, Vipin R. Gavit
article en
2 citations

Abstract

Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes and arenes. This involves: (1) regioselective Ar-H alkylation to form benzhydrylphosphonium salts via a one-pot, four-component reaction with simple reagents and (2) chemoselective reductions or oxidations of the benzylic C-P bond. Notably, reductions with D<sub>2</sub>O yield fully deuterated diarylmethanes. This high-yielding, straightforward approach offers valuable building blocks and enables novel transformations for academic and pharmaceutical research.

Organic LettersVol. 27(14)
Hebrew University of Jerusalem (IL), Center for NanoScience (DE)
Israel Science Foundation, Council for Higher Education
Openalex Percentile: Top 18%
Chemical Reactions and Isotopes
1.58
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Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones — Ahmad Masarwa, Nadim Eghbarieh, et al. · Organic Letters (2025) | TGRS Research Map | TGRS