Reagentless Chemistry "On-Water": An Atom-Efficient and "Green" Route to Cyclic and Acyclic β-Amino Sulfones via aza-Michael Addition Using Microwave Irradiation
Soumik Saha, Amrita Chatterjee* and Mainak Banerjee*
*Department of Chemistry, BITS Pilani-KK Birla Goa Campus, NH 17B Bypass Road, Zuarinagar, Goa 403726, India,
Email: amrita
goa.bits-pilani.ac.in, mainakgoa.bits-pilani.ac.in
S. Saha, A. Chatterjee, M. Banerjee, J. Org. Chem., 2023, 88, 15358-15366.
DOI: 10.1021/acs.joc.3c01855
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Abstract
A double aza-Michael addition of anilines to water-insoluble divinyl sulfones on the surface of water provides solid cyclic β-amino sulfones as easily separable products in excellent yields upon microwave irradiation at 150°C for 10 min. This atom-efficient method converts a broad range of amines and offers good functional group tolerance. Acyclic β-amino sulfones can also be synthesized.
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proposed mechanism
Key Words
N-Heterocycles, S-Heterocycles, Michael addition, Microwave Synthesis
ID: J42-Y2023
