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Synthesis of 2,3‐Disubstituted Indoles by a Rhodium‐Catalyzed Aromatic Amino‐Claisen Rearrangement of N ‐Propargyl Anilines
Author(s) -
Saito Akio,
Kanno Ayumi,
Hanzawa Yuji
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200605162
Subject(s) - aniline , propargyl , claisen rearrangement , cationic polymerization , rhodium , catalysis , ring (chemistry) , chemistry , medicinal chemistry , propane , organic chemistry
Give me a ring! A cationic Rh I 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.