Synthesis of Indole and Biindolyl Triflones: Trifluoromethanesulfonylation of Indoles with Tf2O/TTBP (2,4,6-tri-tert-butylpyridine) System

A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and N-H indole triflones were obtained in 82–96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51–81% yields for the first time by simple treatment of the resulting indole triflones with a base and without a...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 18; pp. 4854 - 4857
Main Authors Xu, Xiu-Hua, Liu, Guo-Kai, Azuma, Ayaka, Tokunaga, Etsuko, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Furans - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Physical Sciences
Pyridines - chemistry
Science & Technology
Stereoisomerism
Sulfonamides - chemistry
Sulfones - chemical synthesis
Sulfones - chemistry
FRIEDEL-CRAFTS ACYLATION
NUCLEOPHILIC TRIFLUOROMETHYLATION
CONVENIENT ROUTE
ONE-POT SYNTHESIS
2-PHOTON ABSORPTION
SULFIDES
EFFICIENT SYNTHESIS
IONIC LIQUID
ARYL
MEDIATED REDUCTIVE TRIFLUOROMETHYLATION
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Summary:A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and N-H indole triflones were obtained in 82–96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51–81% yields for the first time by simple treatment of the resulting indole triflones with a base and without any use of organometallic chemistry. An environmentally friendly solvent, Solkane 365/227, can be substituted for this process without any loss of efficiency.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol201931x