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

Vipin R. Gavit; Nicole Hanania; Nadim Eghbarieh; Israa Shioukhi; Ahmad Masarwa

doi:10.1021/acs.orglett.5c00748

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

Vipin R. Gavit
, Nicole Hanania
, Nadim Eghbarieh
, Israa Shioukhi
, Ahmad Masarwa

Institute of Chemistry

The Hebrew University of Jerusalem

Research output: Contribution to journal › Letter › peer-review

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 D₂O yield fully deuterated diarylmethanes. This high-yielding, straightforward approach offers valuable building blocks and enables novel transformations for academic and pharmaceutical research.

Original language	English
Pages (from-to)	3637-3642
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.5c00748
State	Published - 11 Apr 2025

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c00748

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title = "Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones",

abstract = "Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes and arenes. This involves: (1) regioselective Ar{\textendash}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{\textendash}P bond. Notably, reductions with D2O 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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T1 - Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

AU - Gavit, Vipin R.

AU - Hanania, Nicole

AU - Eghbarieh, Nadim

AU - Shioukhi, Israa

AU - Masarwa, Ahmad

PY - 2025/4/11

Y1 - 2025/4/11

N2 - 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 D2O yield fully deuterated diarylmethanes. This high-yielding, straightforward approach offers valuable building blocks and enables novel transformations for academic and pharmaceutical research.

AB - 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 D2O 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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DO - 10.1021/acs.orglett.5c00748

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JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

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

Abstract

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