Synthesis of Axially Chiral Monofluoroalkenes via Nickel-Catalyzed Reductive Cross-Coupling of gem-Difluoroalkenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-09-13 DOI:10.1021/acs.orglett.4c03119

Tiantian Yin, Ming Jin, Tiantian Zhao, Junbiao Chang, Dachang Bai

引用次数: 0

Abstract

Enantioenriched monofluoroalkenes are important structural motifs in life science and functional materials. To date, only limited strategies were reported for the synthesis of monofluoroalkenes with stereogenic carbon centers; the axially chiral counterpart is still highly desirable. Herein, we report Ni-catalyzed defluorinative cross-electrophile coupling of gem-difluoroalkenes with biaryl electrophiles for the synthesis of axially chiral monofluoroalkenes. The resulting axially chiral monofluoroalkenes are formed with excellent regio- and stereoselectivities. Synthetic transformation of these axially enantioenriched monofluoroalkenes was also demonstrated.

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通过镍催化宝石二氟烯烃的还原交叉偶联合成轴向手性一氟烯烃

对映体一氟烯烃是生命科学和功能材料领域的重要结构主题。迄今为止，关于具有立体碳中心的一氟烯烃合成策略的报道非常有限；轴向手性对应物仍然是非常理想的。在此，我们报告了镍催化的宝石-二氟烯烃与双芳基亲电体的脱氟交-亲电偶联合成轴向手性一氟烯烃的方法。生成的轴向手性单氟烯具有极佳的区域和立体选择性。此外，还展示了这些轴向手性单氟烯的合成转化。

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

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.