Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C­(sp3)– radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen so...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 10; pp. 3848 - 3854
Main Authors Liang, Shengzong, Kumon, Tatsuya, Angnes, Ricardo A, Sanchez, Melissa, Xu, Bo, Hammond, Gerald B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2019
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Chemistry
Chemistry, Organic
Halogenation
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
CATALYSIS
CROSS-COUPLING REACTIONS
OXIDATIVE CHLORINATION
ACTIVATION
SELECTIVE BROMINATION
VISIBLE-LIGHT PHOTOREDOX
H BONDS
GENERATION
REGIOSELECTIVE HYDROCHLORINATION
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Summary:An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C­(sp3)– radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved.
Bibliography:FAPESP
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.9b01337