An organocatalytic photoinduced 1,2-carbofunctionalization strategy for conjugated dienes has been developed. No exogenous photocatalyst or additives are required in this mild protocol and it allows for highly regioselective and efficient 1,2-carboisothiocyanation through the coupling of a diene, an alkyl radical and TMSNCS. The reaction is proposed to proceed through EDA complexation between the diene and TMSNCS.
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http://dx.doi.org/10.1039/d3cc01121f | DOI Listing |
Chemistry
August 2024
Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771, Athens, Greece.
Plastic pollution constitutes an evergrowing urgent environmental problem, since overaccumulation of plastic waste, arising from the immense increase of the production of disposable plastic products, overcame planet's capacity to properly handle them. Chemical upcycling of polystyrene constitutes a convenient method for the conversion of plastic waste into high-added value chemicals, suggesting an attractive perspective in dealing with the environmental crisis. We demonstrate herein a novel, easy-to-perform organocatalytic photoinduced aerobic protocol, which proceeds via synergistic indirect hydrogen atom transfer (HAT) catalysis under LED 390 nm Kessil lamps as the irradiation source.
View Article and Find Full Text PDFOrg Lett
March 2024
Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye, Gansu 734000, P. R. China.
A general catalytic donor for the combination of a photoinduced electron donor-acceptor (EDA) complex and energy transfer was developed. This mild and metal-free protocol allows facile access to various -alkenes. Mechanism studies revealed that the organophotocatalyst, 4-CzIPN, formed a distinct three-component EDA complex with redox-active esters and (CHO)P(O)OH to trigger the photoredox catalysis.
View Article and Find Full Text PDFChem Commun (Camb)
May 2023
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow-226031, India.
An organocatalytic photoinduced 1,2-carbofunctionalization strategy for conjugated dienes has been developed. No exogenous photocatalyst or additives are required in this mild protocol and it allows for highly regioselective and efficient 1,2-carboisothiocyanation through the coupling of a diene, an alkyl radical and TMSNCS. The reaction is proposed to proceed through EDA complexation between the diene and TMSNCS.
View Article and Find Full Text PDFChem Sci
January 2023
Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University Changzhou 213164 China
While asymmetric insertion of metal carbenes into H-X (X = C, N, O, ) bonds has been well-established, asymmetric control over free carbenes is challenging due to the presence of strong background reactions and lack of any anchor for a catalyst interaction. Here we have achieved the first photo-induced metal-free asymmetric H-X bond insertion of this type. With visible light used as a promoter and a chiral phosphoric acid used as a catalyst, α-diazoesters and aryl amines underwent smooth N-H bond insertion to form enantioenriched α-aminoesters with high efficiency and good enantioselectivity under mild conditions.
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August 2022
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University 1139 Shifu Avenue Taizhou 318000 China
An organocatalytic enantioselective radical reaction of potassium alkyltrifluoroborates, DABCO·(SO) and α,β-unsaturated carbonyl compounds under photoinduced conditions is developed, which provides an efficient pathway for the synthesis of chiral β-sulfonyl carbonyl compounds in good yields with excellent enantioselectivity (up to 96% ee). Aside from α,β-unsaturated carbonyl compounds with auxiliary groups, common chalcone substrates are also well compatible with this organocatalytic system. This method proceeds through an organocatalytic enantioselective radical sulfonylation under photoinduced conditions, and represents a rare example of asymmetric transformation involving sulfur dioxide insertion.
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