Fe(III)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes Improved by Using Triphenylphosphate as an Additive

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-10 DOI:10.1002/adsc.202401180

Ye Jin Kim, Dong Bin Kim, So Won Youn

引用次数: 0

Abstract

We herein report that the combination of Fe(OTf)3 and triphenylphosphate (TPP, (PhO)3PO) has proven to be an effective catalyst for the intramolecular hydroamination of amino-1,3-dienes with an efficiency and scope superior to previously reported methods. This catalytic system demonstrated consistent performance with diverse aminodienes as well as aminoolefins, providing five- to seven-membered N-heterocycles. We propose a Lewis/Brønsted acid cocatalysis mechanism involving proton transfer through hydrogen bonding with TPP. Catalyst system consisting of inexpensive and nontoxic iron salt and phosphate additive, relatively low loading and recyclability of catalyst, and rapid and high-yielding reaction are the advantages of this protocol.

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使用三苯基膦作为添加剂改进铁（III）催化的 1,3-二烯分子内氢化反应

我们在此报告，Fe(OTf)3 和磷酸三苯酯（TPP，(PhO)3PO）的组合已被证明是氨基-1,3-二烯分子内氢化的有效催化剂，其效率和范围优于之前报道的方法。该催化体系在处理各种氨基二烯和氨基烯烃时表现出一致的性能，可提供五元到七元的 N- 异环。我们提出了一种路易斯/勃氏酸催化机制，涉及通过与 TPP 的氢键进行质子转移。由廉价无毒的铁盐和磷酸盐添加剂组成的催化剂体系、相对较低的催化剂负载量和催化剂的可回收性以及快速高产的反应是该方案的优势所在。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.