Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-11-13 DOI:10.1016/j.tet.2024.134378
Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie
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Abstract

Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with N-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[b]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.

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用于苯并[b]氮杂卓和 1,3-共轭二烯歧化合成的催化剂控制型可切换形式逆-布赫纳反应
在此,我们成功开发了一种由膦催化剂控制的甲基溴碳酸盐与 N-磺酰基氮杂七烯烃的可切换形式逆-布赫纳反应,该反应提供了一条以中等至高产率获得有价值的苯并[b]氮杂卓和多种取代的 1,3-共轭二烯衍生物的不同而有效的途径。此外,这些方法的特点还包括反应条件温和、不含过渡金属、操作简便、对官能团有广泛的耐受性以及适合克级合成。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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Contents continued Graphical abstract TOC Graphical abstract TOC Editorial Board Synthesis of dendritic self-immolative molecules triggered by reactive electrophilic alkylating agents: Assessment for colorimetric disclosure of such agents
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