催化剂控制的 2-吡啶基噻吩的 C-H 炔基化反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-10-04 DOI:10.1002/adsc.202400856

Yuting Gui, Yaokun Zhao, Xingchi Li, Taoyuan Liang, Shuangliang Zhao, Zhuan Zhang

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引用次数: 0

摘要

介绍了不同的催化剂来克服或增强底物的先天区域选择性。研究发现，铑可通过螯合辅助铑化作用克服先天的 C3 选择性。相反，钯通过亲电钯化作用提高了先天的 C5 选择性。通过这些反应，可以从 2-吡啶基噻吩中生成多种多样的 C3- 和 C5-炔基合成产物。值得注意的是，这种策略被成功地用于直接合成π-扩展官能化的 2-吡啶基噻吩，后者可以转化为更有价值的化合物。

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Catalyst-Controlled Regiodivergent C–H Alkynylation of 2-Pyridylthiophenes

Diﬀerent catalysts are presented to overcome or augment a substrate’s innate regioselectivity. Rhodium was found to overcome the innate C3-selectivity via chelation-assisted rhodation. Conversely, palladium was found to enhance the innate C5-selectivity via electrophilic palladation. These reactions allow for the formation of a diverse range of synthetically versatile C3- and C5-alkynylated products from 2-pyridylthiophenes. Notably, this strategy was successfully employed in the straightforward synthesis of π-extended functionalized 2-pyridylthiophenes, which could be converted into more valuable compounds.

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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.