通过光氧化 C（sp3）-H 烯化反应-邻碘芳基烷醇与炔烃的脱氢反应合成(E)-和(Z)-烯酮的不同方法

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-15 DOI:10.1021/acs.orglett.4c0370710.1021/acs.orglett.4c03707

Liang Zeng, Yin Zhang, Ming Hu*, De-Liang He, Xuan-Hui Ouyang* and Jin-Heng Li*,

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引用次数: 0

摘要

本研究描述了邻碘芳基烷醇与末端炔烃的光氧化 C(sp3)-H 烯化-氢化反应，用于合成 (E)- 和 (Z)- 含季碳中心的戊-4-烯-1-酮。立体选择性取决于炔烃和光催化剂的使用。使用 4-DPAIPN 等有机光催化剂可以操纵邻碘芳基烷醇与芳基炔的 C(sp3)-H 烯化-氢化反应，从而生成 (E)-戊-4-烯-1-酮；而使用 Ir(ppy)2(dtbbpy)PF6 等 Ir 钾催化剂则可以与芳基炔反应生成 (Z)-戊-4-烯-1-酮。对于烷基炔，只有在 4-DPAIPN 或 Ir(ppy)2(dtbbpy)PF6存在的情况下，反应才能生成 (E)-戊-4-烯-1-酮。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Divergent Synthesis of (E)- and (Z)-Alkenones via Photoredox C(sp3)–H Alkenylation–Dehydrogenation of o-Iodoarylalkanols with Alkynes

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Divergent Synthesis of (E)- and (Z)-Alkenones via Photoredox C(sp3)–H Alkenylation–Dehydrogenation of o-Iodoarylalkanols with Alkynes

A photoredox C(sp³)–H alkenylation–dehydrogenation of o-iodoarylalkanols with terminal alkynes for the synthesis of (E)- and (Z)-quaternary carbon center-containing pent-4-en-1-ones is described. The stereoselectivity depends on the utilization of alkynes and photocatalysts. While using an organic photocatalyst like 4-DPAIPN manipulates the C(sp³)–H alkenylation–dehydrogenation of o-iodoarylalkanols with arylalkynes to assemble (E)-pent-4-en-1-ones, in the case of an Ir potocatalyst such as Ir(ppy)₂(dtbbpy)PF₆ the reaction with arylalkynes delivers (Z)-pent-4-en-1-ones. For alkylalkynes, the reaction furnishes (E)-pent-4-en-1-ones exclusively in the presence of 4-DPAIPN or Ir(ppy)₂(dtbbpy)PF₆.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.