Halodealkenylation: Ozonolysis and Catalytic FeII with Vitamin C Convert C(sp3)–C(sp2) Bonds to C(sp3)–Halide Bonds

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-09 DOI:10.1021/acs.orglett.4c0408410.1021/acs.orglett.4c04084

Brady W. Dehnert, Youwei Yin and Ohyun Kwon*,

引用次数: 0

Abstract

As part of our investigations into C–C bond scission and functionalization, we report a halodealkenylation in which the C(sp³)–C(sp²) bonds of alkenes are cleaved and C(sp³)–halide bonds are formed, via a radical intermediate. These transformations occur through Criegee ozonolysis and Fe^II-catalyzed reductive coupling assisted by vitamin C as a stoichiometric reductant. We applied this strategy to the formal synthesis of (R,R,R)-γ-tocopherol.

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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.