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将醛转化为不对称(氘代)二芳基甲烷和二芳基酮的可编程策略。

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

作者信息

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

机构信息

Institute of Chemistry, The Center for Nanoscience and Nanotechnology, and Casali Center for Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel.

出版信息

Org Lett. 2025 Apr 11;27(14):3637-3642. doi: 10.1021/acs.orglett.5c00748. Epub 2025 Mar 28.

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

摘要

在此,我们展示了一种从醛和芳烃合成不对称二芳基甲烷和二芳基酮的通用方法。这涉及:(1) 通过与简单试剂的一锅四组分反应进行区域选择性Ar-H烷基化以形成二苯甲基鏻盐,以及(2) 苄基C-P键的化学选择性还原或氧化。值得注意的是,用DO还原可得到完全氘代的二芳基甲烷。这种高产率、直接的方法提供了有价值的结构单元,并为学术和药物研究实现了新的转化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a624/11998069/bf917444a681/ol5c00748_0001.jpg

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