Gold- and Indium-Catalyzed Synthesis of 3- and 6-Sulfonylindoles from ortho-Alkynyl-N-sulfonylanilines

Consecutive formation of CN and CS bonds: The gold‐catalyzed intramolecular aminosulfonylation of 2‐alkynyl‐N‐sulfonylanilines 1 (R1=H) produces 3‐sulfonylindoles 2 in good to high yields, whereas the indium‐catalyzed aminosulfonylation of 2‐alkynyl‐6‐methoxy‐N‐sulfonylanilines 1 (R1=MeO) affords...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-01, Vol.46 (13), p.2284-2287
Main Authors: Nakamura, Itaru, Yamagishi, Uichiro, Song, Dschun, Konta, Sayaka, Yamamoto, Yoshinori
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
cyclization
fused-ring systems
gold
Gold - chemistry
indium
Indium - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Sulfur Acids - chemical synthesis
Sulfur Acids - chemistry
synthetic methods
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Summary:Consecutive formation of CN and CS bonds: The gold‐catalyzed intramolecular aminosulfonylation of 2‐alkynyl‐N‐sulfonylanilines 1 (R1=H) produces 3‐sulfonylindoles 2 in good to high yields, whereas the indium‐catalyzed aminosulfonylation of 2‐alkynyl‐6‐methoxy‐N‐sulfonylanilines 1 (R1=MeO) affords 6‐sulfonylindoles 3 as the major products (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200604038