Palladium-Catalyzed Decarboxylative Benzylation and Allylation of Six-Membered Endocyclic Enecarbamates

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-15 DOI:10.1002/adsc.202401140

Junhao Ruan, Xi Cao, Yipeng Zhou, Xiaoyu Yang, Weijie Chen

引用次数: 0

Abstract

Six-membered endocyclic benzyl/allyl enecarbamates undergo a Pd-catalyzed decarboxylation process to generate endocyclic 1-azaallyl anions and Pd–benzyl/allyl cations. The ion pair then react with each other followed by reduction to ultimately give unprotected -2-(hetero)aryl-3-benzylpiperidines and 2-(hetero)aryl-3-allylpiperidines in 31−91% yields as single cis-diastereomers. These reactions represent a strategy to form unprotected β-substituted piperidines, which generates elusive endocyclic 1-azaallyl anion intermediates by introducing the negative charge from the N-terminal.

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钯催化的六元内环烯碳酰胺的脱羧苄化和烯丙基化反应

六元内环苄基/烯丙基萘甲酸酯经过钯催化的脱羧过程，生成内环 1-azaallyl 阴离子和钯-苄基/烯丙基阳离子。然后，离子对相互反应并还原，最终以 31-91% 的产率得到未受保护的 -2-（杂）芳基-3-苄基哌啶和 2-（杂）芳基-3-烯丙基哌啶，它们是单一的顺式-非对映异构体。这些反应代表了一种形成无保护 β-取代哌啶的策略，通过从 N 端引入负电荷，生成难以捉摸的内环 1-氮杂烯丙基负离子中间体。

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.