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Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion
Author(s) -
Hussein Mohanad A.,
Tran Uyen P. N.,
Huynh Vien T.,
Ho Junming,
Bhadbhade Mohan,
Mayr Herbert,
Nguyen Thanh V.
Publication year - 2020
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.201910578
Subject(s) - chemistry , carbanion , nucleophile , bromide , regioselectivity , michael reaction , halide , adduct , nucleophilic addition , photochemistry , amine gas treating , addition reaction , phosphine , organic chemistry , medicinal chemistry , polymer chemistry , catalysis
Tropylium bromide undergoes noncatalyzed, regioselective additions to a large variety of Michael acceptors. In this way, acrylic esters are converted into β‐bromo‐α‐cycloheptatrienylpropionic esters. The reactions are interpreted as nucleophilic attack of bromide ions at the electron‐deficient olefins and the approach of the tropylium ion to the incipient carbanion. Quantum chemical calculations were performed to elucidate the analogy to the amine‐ or phosphine‐catalyzed Rauhut–Currier reactions. Subsequent synthetic transformations of the bromo‐cycloheptatrienylated adducts are reported.