Direct Conversion of Alcohols to α‑Chloro Aldehydes and α‑Chloro Ketones

Direct Conversion of Alcohols to α‑Chloro Aldehydes and α‑Chloro Ketones

Direct conversion of primary and secondary alcohols into the corresponding α-chloro aldehydes and α-chloro ketones using trichloroisocyanuric acid, serving both as stoichiometric oxidant and α-halogenating reagent, is reported. For primary alcohols, TEMPO has to be added as an oxidation catalyst, an...

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Veröffentlicht in:Organic letters 2014-09, Vol.16 (18), p.4932-4935
Hauptverfasser: Jing, Yuanyuan, Daniliuc, Constantin G, Studer, Armido
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Aldehydes - chemical synthesis
Aldehydes - chemistry
Catalysis
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Oxidants
Oxidation-Reduction
Stereoisomerism
Triazines - chemistry
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Beschreibung
Zusammenfassung:Direct conversion of primary and secondary alcohols into the corresponding α-chloro aldehydes and α-chloro ketones using trichloroisocyanuric acid, serving both as stoichiometric oxidant and α-halogenating reagent, is reported. For primary alcohols, TEMPO has to be added as an oxidation catalyst, and for the transformation of secondary alcohols (TEMPO-free protocol), MeOH as an additive is essential to promote chlorination of the intermediary ketones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5024568