In this work, we report a protocol for the synthesis of an indoloquinolinone skeleton using visible light-induced energy transfer. This method avoids the premodification of substrates and exhibits high yields. For gram-scale reactions, only 0.01 mol % (100 ppm) of photosensitizer is required for rapid conversion. Mechanistic studies revealed that this reaction differs from conventional 6π photocyclization reactions; undergoing a process involving 6π cyclization due to energy transfer and dehydrogenation due to product self-catalysis has been experienced.
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http://dx.doi.org/10.1021/acs.joc.4c01653 | DOI Listing |
Org Lett
January 2025
Faculty of Chemistry, University of Wrocław, Joliot-Curie 14 Street, 50-383 Wrocław, Poland.
Studies presenting visible-light-induced desulfurization of peptides containing a cysteine residue have been carried out. This transformation driven by light-emitting-diode-type light proceeds with high efficiency in an aqueous solution at room temperature and involves the use of a catalytic amount of photosensitizer, Rose Bengal. The procedure has been tested on model synthetic peptides, lysozyme C and α-crystallin, and successfully applied to a one-pot native chemical ligation (NCL)-desulfurization protocol.
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January 2025
Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China.
Vicinal bis(tetraarylphosphonium) salts have scarcely been reported in the literature. In this study, we demonstrate that visible-light-induced difunctionalization of -trifluoromethylsulfonylated diaryliodonium salts conveniently furnishes bis(phosphonium) salts without additional catalysts or photoinitiators. The methodology establishes a practical platform for the preparation of bis(phosphonium) salts using readily available tertiary phosphines.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced insertion of siloxycarbene into amide N-H bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions with a broad range of secondary N-H amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable - and -acetals in excellent isolated yields.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Sichuan University, West China School of Pharmacy, Renmin Sout Road, 3rd Section, 17#, 610041, Chengdu, CHINA.
Bryostatins are a family of marine natural products that have garnered significant interests, as evidenced by over 40 clinical trials. However, their extremely low natural abundance has severely limited further research. Despite significant efforts, which have led to the total synthesis of seven bryostatin members by eight independent research groups, these complex molecules present persistent challenges for stereocontrolled, large-scale, and especially divergent synthesis.
View Article and Find Full Text PDFHeliyon
January 2025
Institute of Chemical Sciences, University of Swat, Swat, 19120, Khyber Pakhtunkhwa, Pakistan.
In recent years, antibiotic pollution has become a major environmental concern. The extensive production and widespread use of prescribed antibiotics have significantly impacted ecosystems. The main objective of the present study is to investigate the photocatalytic degradation of the antibiotic norfloxacin (NFX) under visible light.
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