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 › Article › 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
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c00748
State	Accepted/In press - 2025

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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-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.",

author = "Gavit, {Vipin R.} and Nicole Hanania and Nadim Eghbarieh and Israa Shioukhi and Ahmad Masarwa",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c00748",

language = "الإنجليزيّة",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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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

Y1 - 2025

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.

UR - http://www.scopus.com/inward/record.url?scp=105001726899&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5c00748

DO - 10.1021/acs.orglett.5c00748

M3 - مقالة

C2 - 40155201

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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