Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols

Zhu, Haiqian; Zheng, Hanliang; Zhang, Junhua; Feng, Jian; Kong, Lichun; Zhang, Fang; Xue, Xiao‐Song; Zhu, Gangguo

doi:10.1039/d1sc03416b

Cited by 15 publications

(2 citation statements)

References 71 publications

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“…Xue and Zhu found a divergent reaction of alkynylaldehyde 20 - 1 with tosyl chloride ( 20 - 2 ) (Scheme ). When tosyl chloride ( 20 - 2 ) reacts with alkynylaldehyde 20 - 1 in DMA in the presence of Ir(ppy) 3 , the five-membered ring forming reaction proceeds to give product 20 - 3 . On the other hand, when the reaction solvent was changed to MeCN, compound 20 - 4 bearing a six-membered ring scaffold became the main product.…”

Section: Conditions-controlled Divergent Reactionsmentioning

confidence: 99%

Switchable Divergent Synthesis Using Photocatalysis

2022

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A highly selective and divergent synthesis enables access to various molecules and has garnered broad interest from not only organic chemists but also medicinal chemists and biologists who work with chemical libraries. Since the 20th century, such divergent transformations have been achieved using transition-metal-catalyzed reactions, in which the choice of catalyst or ligand crucially affects the selectivity. Over the past several decades, photocatalysts have attracted a considerable amount of attention because they provide additional ways to control the reaction intermediates and product selectivity via electron or energy transfer. From this perspective, we highlight the recent development of switchable and divergent syntheses using photocatalysts, which are difficult to achieve using classical catalytic transformations.

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Section: Conditions-controlled Divergent Reactionsmentioning

confidence: 99%

Switchable Divergent Synthesis Using Photocatalysis

2022

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“…Cyclopentenones are important constituents of a number of natural products, functional materials, and pharmaceuticals. 1 As such, the synthesis of these privileged frameworks has attracted considerable attention, 1–3 including Nazarov cyclization 1 c and Pauson–Khand reaction. 2 On the other hand, radical addition–translocation–cyclization (RATC) of alkynes has become an attractive method for the efficient build-up of synthetically important five-membered rings.…”

Section: Introductionmentioning

confidence: 99%

Access to cyclopentenonesviacopper-catalyzed 5-endotrifluoromethylcarbocyclization of ynones

Bai

Qiu

et al. 2022

Org. Chem. Front.

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Photoredox and Copper‐Catalyzed Sulfonylphosphorothiolation of Alkenes toward β‐Sulfonyl Phosphorothioates

Zhu

Liu

et al. 2022

Adv Synth Catal

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A photoredox and copper‐catalyzed sulfonylphosphorothiolation of alkenes has been developed. With the use of readily available aryl or alkyl sulfonyl chlorides as radical precursors and (RO)2P(O)SH as coupling partners, a wide range of decorated β‐sulfonyl phosphorothioates could be obtained in 37–98% yields with good functional group tolerance. Importantly, this three‐component reaction can be conveniently extended to late‐stage modification of bioactive molecules and gram‐scale synthesis.

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Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols

Abstract: Divergent synthesis is a powerful strategy for the fast assembly of different molecular scaffolds from the identical starting materials. We describe here a solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes...

Cited by 15 publications

References 71 publications

Switchable Divergent Synthesis Using Photocatalysis

Switchable Divergent Synthesis Using Photocatalysis

Access to cyclopentenonesviacopper-catalyzed 5-endotrifluoromethylcarbocyclization of ynones

Photoredox and Copper‐Catalyzed Sulfonylphosphorothiolation of Alkenes toward β‐Sulfonyl Phosphorothioates

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