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Mechanistic Study of Domino Processes Involving the Bidentate Lewis Acid Catalyzed Inverse Electron‐Demand Diels−Alder Reaction
Author(s) -
Strauss Marcel A.,
Kohrs Daniel,
Ruhl Julia,
Wegner Hermann A.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100486
Subject(s) - chemistry , domino , lewis acids and bases , catalysis , amine gas treating , diels–alder reaction , ring (chemistry) , naphthalene , combinatorial chemistry , denticity , lewis acid catalysis , cascade reaction , organic chemistry , metal
The detailed understanding of mechanisms is the basis to design new reactions. Herein, we studied the domino bidentate Lewis acid catalyzed inverse electron‐demand Diels−Alder (IEDDA) reaction developed in our laboratory computationally as well as by synthetic experiments, to characterize different pathways. A quinodimethane intermediate was identified as key structure, which is the basis for all subsequent transformations: Elimination to an aromatic naphthalene, rearrangement to a dihydroaminonaphthalene and a photo‐induced ring opening. These insights allow to optimize the reaction conditions, such as catalytic utilization of amine, as well as to advance new reactions in the future.