期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 37, 页码 20543-20550出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202106183
关键词
carbon nitride; chromoselective catalysis; organic synthesis; photoredox catalysis; sulfonyl chloride
资金
- Max Planck Society
- Projekt DEAL
Photocatalysis utilizes different colors of excitation light to selectively convert S-arylthioacetates into three different products. Factors such as negatively charged polyanion, positive valence band potential, intraband states, singlet oxygen sensitization, and multi-electron transfer contribute to this chromoselective conversion.
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one-light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
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