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. 2024 Apr 5;15(17):6515-6521.
doi: 10.1039/d4sc01355g. eCollection 2024 May 1.

Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade

Xingchen Ye  1 , Huaijin Pan  1 , Yong Huang  2 , Jiean Chen  3 , Zhaofeng Wang  1
Affiliations

Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade

Xingchen Ye et al. Chem Sci. .

Abstract

Construction of complex molecular skeletons with ubiquitous chemical feedstocks in a single transformation is highly appealing in organic synthesis. We report a novel visible-light-induced three-component reaction for the construction of complex 2,4,5-trisubstituted oxazoles, which are valuable in medicinal chemistry, from simple and readily available iodonium-phosphonium hybrid ylides, carboxylic acids, and nitriles. This reaction features a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade, in which a photo-generated α-phosphonium carbene acts as a sequence trigger. This catalyst- and additive-free transformation exhibits high efficiency and broad substrate scope for synthesizing diverse oxazoles.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Fig. 1
Fig. 1. Introduction. (A) Representative bioactive molecules containing tri-substituted oxazole motifs. (B) MCRs for the synthesis of oxazoles via a P/N hybrid ylide formation/trapping cascade.
Fig. 2
Fig. 2. Mechanistic studies. (A) 18O-Labeling experiment. (B) Step-wise experiment. (C) Control experiment. (D) Possible mechanism.
See this image and copyright information in PMC

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