钯催化丙胺和1,3 -二烯的环化胺化反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-01-09 DOI:10.1002/adsc.202401464

Biao Yao, Wenfang Xiong, Wanqing Wu, Huanfeng Jiang

{"title":"钯催化丙胺和1,3 -二烯的环化胺化反应","authors":"Biao Yao, Wenfang Xiong, Wanqing Wu, Huanfeng Jiang","doi":"10.1002/adsc.202401464","DOIUrl":null,"url":null,"abstract":"A novel and efficient palladium‐catalyzed cyclization amination of propargylamines and 1,3‐dienes is reported for the first time, yielding a series of chloromethylene pyrrolidines with high efficiency and excellent selectivity. This method was successfully applied to the late‐stage modification of natural products and drug molecules, providing molecular backbones with potential applications. The reaction was shown to achieve regioselective modulation of the product molecules through the resonance between the solvent and allylpalladium. Additionally, the E‐form products were found to be thermodynamically stable.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"56 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium‐Catalyzed Cyclization Amination of Propargylamine and 1,3‐Dienes\",\"authors\":\"Biao Yao, Wenfang Xiong, Wanqing Wu, Huanfeng Jiang\",\"doi\":\"10.1002/adsc.202401464\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A novel and efficient palladium‐catalyzed cyclization amination of propargylamines and 1,3‐dienes is reported for the first time, yielding a series of chloromethylene pyrrolidines with high efficiency and excellent selectivity. This method was successfully applied to the late‐stage modification of natural products and drug molecules, providing molecular backbones with potential applications. The reaction was shown to achieve regioselective modulation of the product molecules through the resonance between the solvent and allylpalladium. Additionally, the E‐form products were found to be thermodynamically stable.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"56 1\",\"pages\":\"\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2025-01-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202401464\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401464","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

摘要

本文首次报道了一种新颖高效的钯催化丙炔胺和1,3二烯的环化胺化反应，得到了一系列效率高、选择性好的氯亚甲基吡咯烷。该方法已成功应用于天然产物和药物分子的后期修饰，为分子骨架提供了潜在的应用前景。该反应通过溶剂与烯丙基钯之间的共振实现了产物分子的区域选择性调制。此外，E - form产物是热力学稳定的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Palladium‐Catalyzed Cyclization Amination of Propargylamine and 1,3‐Dienes

A novel and efficient palladium‐catalyzed cyclization amination of propargylamines and 1,3‐dienes is reported for the first time, yielding a series of chloromethylene pyrrolidines with high efficiency and excellent selectivity. This method was successfully applied to the late‐stage modification of natural products and drug molecules, providing molecular backbones with potential applications. The reaction was shown to achieve regioselective modulation of the product molecules through the resonance between the solvent and allylpalladium. Additionally, the E‐form products were found to be thermodynamically stable.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

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.