Premium
Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl Rh III Complex
Author(s) -
Yamada Takayuki,
Shibata Yu,
Kawauchi Susumu,
Yoshizaki Soichi,
Tanaka Ken
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801125
Subject(s) - annulation , catalysis , cascade , cyclopentadienyl complex , chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , chromatography
It has been established that a cyclopentadienyl Rh III complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N ‐pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C−H bond cleavage, alkyne insertion, and the formal Lossen rearrangement.