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

Yicen Ge, Hui Yang, Arne Heusler, Zhijie Chua, Ming Wah Wong, Choon‐Hong Tan

Chemistry - An Asian Journal · 2019 · 33 citations · 45 references

Concepts

Abstract

Abstract 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.

References

45