Copper-Catalyzed Reductive Coupling of Nitroalkanes with Aliphatic Grignard/Cerium and Organozinc Reagents for Synthesis of Functionalized Nitrones

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-12-23 DOI:10.1002/adsc.202401259
Takeshi Hata, Koki Nishi, Koki Yamaguchi, Yuta Tatsumi, Naomi Tanaka, Masayuki Shigeta, Hirokazu Urabe
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引用次数: 0

Abstract

This study aims to develop a more efficient, functional-group-tolerant approach using stable nitroalkanes and reductive coupling reactions with aliphatic Grignard/cerium and organozinc reagents. The treatment of nitroalkanes with aliphatic Grignard reagents in the presence of a catalytic amount of CuF<sub>2</sub> and stoichiometric amount of CeCl<sub>3</sub> affords various nitrones in good yields as single isomers. The reaction of tertiary nitroalkanes with organozinc reagents affords various functionalized nitrones without CuF<sub>2</sub> or CeCl<sub>3</sub>. These reductive coupling reactions proceed without the loss of functional groups such as alkene, alkyne, benzyl ether, chlorine, ester, and nitrile moieties. Nitrones can also be used as precursors for [3+2] cyclizations with electron-withdrawing alkenes and alkynes.
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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