亚磷酸钠的还原性胺化反应：底物指南。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-28 DOI:10.1021/acs.joc.5c00962

Artemy R Fatkulin,Vasily A Korochantsev,Evgeniya S Podyacheva,Fedor S Kliuev,Olesya V Zvereva,Mikhail A Losev,Alexey N Rodionov,Ivan V Smirnov,Maria I Godovikova,Oleg I Afanasyev,Denis A Chusov

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引用次数: 0

摘要

还原胺化反应是合成有机化学的重要手段。最近，次亚磷酸钠作为一种有前途的还原剂的适用性已被证明。然而，这些工作中使用的底物有限，无法可靠地评估从不同性质的起始材料合成胺的方法的多功能性。在此，我们报道了在无催化剂还原胺化中使用NaH2PO2的全面研究。发现了适合不同类别胺和羰基化合物的各种组合的反应条件，并揭示了该工艺的局限性。该研究包括反应动力学的阐明，并建立了胺亲核性与反应结果之间的关系。

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Reductive Amination Reactions Using Sodium Hypophosphite: a Guide to Substrates.

The reactions of reductive amination are of paramount importance as tools of synthetic organic chemistry. Recently, the applicability of sodium hypophosphite as a promising reductant for such reactions has been demonstrated. However, the limited set of substrates used in those works does not allow for a reliable evaluation of the versatility of the approach for synthesizing amines from starting materials of different natures. Herein, we report a comprehensive study of using NaH2PO2 in the catalyst-free reductive amination. Reaction conditions suitable for various combinations of different classes of amines and carbonyl compounds have been discovered, and limitations of the process have been revealed. The study includes reaction kinetics elucidation, and the relationship between amine nucleophilicity and the outcome of this reaction has been established.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.