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Halogen‐Bonding‐Induced Conjugate Addition of Thiophenes to Enones and Enals
Author(s) -
Ge YiCen,
Yang Hui,
Heusler Arne,
Chua Zhijie,
Wong Ming Wah,
Tan ChoonHong
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900607
Subject(s) - trifluoromethanesulfonate , conjugate , halogen , catalysis , chemistry , halogen bond , thiophene , alkylation , salt (chemistry) , polymer chemistry , medicinal chemistry , organic chemistry , mathematical analysis , alkyl , mathematics
Herein, we report the conjugate addition of α,β‐unsaturated carbonyl compounds to thiophene derivatives. We used a 2‐iodoimidazolinium triflate salt as a halogen‐bonding donor, which afforded moderate‐to‐excellent yields of the corresponding alkylated thiophenes. Insight into the catalytic process was obtained from 1 H NMR spectroscopy studies and DFT calculations, which indicated a halogen‐bonding‐supported mechanism with limited Brønsted acid catalysis.