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A Simple and Efficient Method for the Preparation of α‐Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant
Author(s) -
Tang ShiZhong,
Zhao Wenshuang,
Chen Tao,
Liu Yang,
Zhang XiaoMing,
Zhang FuMin
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700833
Subject(s) - chemistry , halogen , reagent , bromide , ketone , halogenation , yield (engineering) , iron(iii) chloride , chloride , combinatorial chemistry , substrate (aquarium) , chemoselectivity , organic chemistry , catalysis , alkyl , materials science , oceanography , metallurgy , geology
α‐Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α‐halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three‐step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram‐scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments.