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

被引：3

作者：

Dehnert, Brady W. ^{[1
]}

Yin, Youwei ^{[1
]}

Kwon, Ohyun ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 50期

基金：

美国国家卫生研究院;

关键词：

CARBON-CENTERED RADICALS; ABSOLUTE RATE CONSTANTS; HALOGEN ABSTRACTION; ALPHA-TOCOPHEROL; THIYL RADICALS; HYDROCHLORINATION; STEREOCHEMISTRY; KINETICS; ALKENES; IODINE;

D O I：

10.1021/acs.orglett.4c04084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 FeII-catalyzed reductive coupling assisted by vitamin C as a stoichiometric reductant. We applied this strategy to the formal synthesis of (R,R,R)-gamma-tocopherol.

引用

页码：10921 / 10927

页数：7

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