基于[1,2]-Phospha-Brook重排/ Brønsted碱基环化策略的形式[3+2]环加成模块化合成2,3,4,6-四取代噻吩[2,3-c]呋喃

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-03-26 DOI:10.1002/adsc.202500255

Azusa Kondoh, Kohei Aita, Masahiro Terada

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引用次数: 0

摘要

已经建立了2,3,4,6-四取代噻吩[2,3-c]呋喃的模块化合成方法，该方法采用了正式的[3+2]环加成，利用[1,2]-磷酸-布鲁克重排和随后的Brønsted碱基介导的环化，从而有效地获得了广泛的密集功能化噻吩[2,3-c]呋喃，否则难以合成。该方法也适用于2,3,4,6-四取代硒代[2,3-c]呋喃的合成，并可推广到六取代苯并噻吩的合成。

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Modular Synthesis of 2,3,4,6-Tetrasubstituted Thieno[2,3-c]furans Based on Formal [3+2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement / Brønsted Base-Mediated Cyclization Strategy

A modular synthesis of 2,3,4,6-tetrasubstituted thieno[2,3-c]furans, which employs a formal [3+2] cycloaddition utilizing the [1,2]-phospha-Brook rearrangement and a subsequent Brønsted base-mediated cyclization, has been established, providing an efficient access to a wide range of densely functionalized thieno[2,3-c]furans that are otherwise difficult to synthesize. This method is also applicable to the synthesis of 2,3,4,6-tetrasubstituted selenolo[2,3-c]furans and can be extended to the synthesis of hexasubstituted benzothiophenes.

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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.