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Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

ABSTRACT: 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.

SUBMITTER: Liang S

PROVIDER: S-EPMC6525078 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

Liang Shengzong S Kumon Tatsuya T Angnes Ricardo A RA Sanchez Melissa M Xu Bo B Hammond Gerald B GB

Organic letters 20190503 10

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. ...[more]

PMID: 31050440

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