Photocatalytic selective synthesis of ()-β-aminovinyl sulfones and ()-β-amidovinyl sulfones using Ru(bpy)Cl as the catalyst

Selectively producing a variety of valuable compounds using controlled chemical reactions starting from a common material is an appealing yet complex concept. Herein, a photocatalytic approach for the selective synthesis of ( E )-β-aminovinyl sulfones and ( E )-β-amidovinyl sulfones from allenamides...

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Published in:RSC advances 2024-01, Vol.14 (1), p.7-76
Main Authors: Huang, Yu-Wen, Li, Jia-Zhuo, Yang, Feng, Zhang, Xi-Yu, Wang, Yan-Jing, Meng, Xin-Chao, Leng, Bo-Rong, Wang, De-Cai, Zhu, Yi-Long
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Summary:Selectively producing a variety of valuable compounds using controlled chemical reactions starting from a common material is an appealing yet complex concept. Herein, a photocatalytic approach for the selective synthesis of ( E )-β-aminovinyl sulfones and ( E )-β-amidovinyl sulfones from allenamides and sodium sulfinates was established. This reaction exhibits the traits of an eco-friendly solvent and adjustable amide cleavage, and can accommodate a diverse range of substrates with exceptional functional group tolerance. Based on control experiments and deuterium labeling experiments, a plausible radical reaction pathway is proposed. A photocatalytic strategy has been developed for the selective synthesis of ( E )-β-aminovinyl sulfones and ( E )-β-amidovinyl sulfones through the utilization of allenamides and sodium sulfinates.
ISSN:2046-2069
DOI:10.1039/d3ra08272e