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[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium‐Catalyzed Process by Tuning the Cp Ligand
Author(s) -
Hong Seung Youn,
Jeong Jisu,
Chang Sukbok
Publication year - 2017
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.201612559
Subject(s) - rhodium , annulation , ligand (biochemistry) , chemistry , cyclopentadienyl complex , catalysis , conjugated system , medicinal chemistry , product distribution , catalytic cycle , combinatorial chemistry , stereochemistry , organic chemistry , receptor , biochemistry , polymer
A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium‐catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp‐bound rhodium species.