Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 21; pp. 5484 - 5487
Main Authors Motiwala, Hashim F, Vekariya, Rakesh H, Aubé, Jeffrey
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.11.2015
Amer Chemical Soc
Subjects
Acylation
Catalysis
Chemistry
Chemistry, Organic
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Physical Sciences
Propanols - chemistry
Science & Technology
Stereoisomerism
ACID
FLUORINATED ALCOHOLS
CATALYST
ALKYLATION
CHLORIDE
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Summary:Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02851