Synthesis of 2,3-Disubstituted Indoles by a Rhodium-Catalyzed Aromatic Amino-Claisen Rearrangement of N-Propargyl Anilines

Give me a ring! A cationic RhI catalyst promotes the formation of fused arenes containing a five‐membered ring (see scheme) by an aromatic amino‐Claisen rearrangement of N‐propargyl aniline derivatives in refluxing hexafluoro‐2‐propanol (HFIP). cod=1,5‐cyclooctadiene, dppp=1,3‐bis(diphenylphosphanyl...

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Published inAngewandte Chemie International Edition Vol. 46; no. 21; pp. 3931 - 3933
Main Authors Saito, Akio, Kanno, Ayumi, Hanzawa, Yuji
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
Alkynes - chemistry
Amino Acids, Aromatic - chemistry
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
cyclization
heterocycles
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
rearrangement
rhodium
Rhodium - chemistry
Science & Technology
Stereoisomerism
CYCLOADDITION REACTIONS
ANNULATION
alkynes
COMPLEXES
INTERNAL ALKYNES
cyclization
HETEROCYCLIC SYNTHESIS
heterocycles
ETHER
CYCLOISOMERIZATION
DERIVATIVES
rearrangement
HYDROARYLATION
rhodium
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Summary:Give me a ring! A cationic RhI catalyst promotes the formation of fused arenes containing a five‐membered ring (see scheme) by an aromatic amino‐Claisen rearrangement of N‐propargyl aniline derivatives in refluxing hexafluoro‐2‐propanol (HFIP). cod=1,5‐cyclooctadiene, dppp=1,3‐bis(diphenylphosphanyl)propane, Tf=trifluoromethanesulfonyl.
Bibliography:This work was supported by a Grant-in-Aid for Young Scientists (B) from MEXT, Japan (grant No. 17790021). A generous donation of HFIP by Central Glass Co., Ltd. is gratefully acknowledged.
istex:117D044343BE723E659EA646EB8FA58F11212C93
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MEXT, Japan - No. 17790021
ArticleID:ANIE200605162
This work was supported by a Grant‐in‐Aid for Young Scientists (B) from MEXT, Japan (grant No. 17790021). A generous donation of HFIP by Central Glass Co., Ltd. is gratefully acknowledged.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200605162