Halogen‐Bonding‐Induced Conjugate Addition of Thiophenes to Enones and Enals

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 w...

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Published inChemistry, an Asian journal Vol. 14; no. 15; pp. 2656 - 2661
Main Authors Ge, Yi‐Cen, Yang, Hui, Heusler, Arne, Chua, Zhijie, Wong, Ming Wah, Tan, Choon‐Hong
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 01.08.2019
Subjects
Alkylation
Bonding
Carbonyl compounds
Carbonyls
Catalysis
Chemistry
conjugate addition
Conjugates
density functional calculations
halogens
NMR spectroscopy
sulfur heterocycles
synthetic methods
Thiophenes
density functional calculations
halogens
conjugate addition
synthetic methods
sulfur heterocycles
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Summary: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 1H NMR spectroscopy studies and DFT calculations, which indicated a halogen‐bonding‐supported mechanism with limited Brønsted acid catalysis. Halo: Bonding Evolved. The conjugate addition of α,β‐unsaturated enones and enals to thiophene derivatives afforded the corresponding alkylated thiophenes in moderate‐to‐excellent yields. This reaction was catalyzed by halogen‐bonding interactions with a 2‐iodoimidazolinium triflate salt as a soft Lewis acid and halogen‐bond donor.
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ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201900607