{"title":"芳香醛和末端炔光催化合成吲哚酮的研究。","authors":"Florence Babawale, , , Indrajit Ghosh*, , and , Burkhard König*, ","doi":"10.1021/acs.joc.5c01749","DOIUrl":null,"url":null,"abstract":"<p >Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transition-metal catalysis, prefunctionalized substrates, and multiple redox steps. Herein, we report a photochemical C–H annulation strategy for the direct synthesis of indanones from simple, unmodified aromatic aldehydes and terminal alkynes. The reaction proceeds under 365 nm light using tetrabutylphosphonium decatungstate ([Bu<sub>4</sub>P]<sub>4</sub>W<sub>10</sub>O<sub>32</sub>, TBPDT) as a hydrogen atom transfer (HAT) photocatalyst. This prefunctionalization-free protocol tolerates a broad range of substrates, eliminates the need for additional redox steps, and expands the toolbox for sustainable indanone synthesis.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 39","pages":"13885–13890"},"PeriodicalIF":3.6000,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c01749","citationCount":"0","resultStr":"{\"title\":\"Photo-Catalyzed Synthesis of Indanones from Aromatic Aldehydes and Terminal Alkynes\",\"authors\":\"Florence Babawale, , , Indrajit Ghosh*, , and , Burkhard König*, \",\"doi\":\"10.1021/acs.joc.5c01749\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transition-metal catalysis, prefunctionalized substrates, and multiple redox steps. Herein, we report a photochemical C–H annulation strategy for the direct synthesis of indanones from simple, unmodified aromatic aldehydes and terminal alkynes. The reaction proceeds under 365 nm light using tetrabutylphosphonium decatungstate ([Bu<sub>4</sub>P]<sub>4</sub>W<sub>10</sub>O<sub>32</sub>, TBPDT) as a hydrogen atom transfer (HAT) photocatalyst. This prefunctionalization-free protocol tolerates a broad range of substrates, eliminates the need for additional redox steps, and expands the toolbox for sustainable indanone synthesis.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 39\",\"pages\":\"13885–13890\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-09-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c01749\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c01749\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c01749","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Photo-Catalyzed Synthesis of Indanones from Aromatic Aldehydes and Terminal Alkynes
Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transition-metal catalysis, prefunctionalized substrates, and multiple redox steps. Herein, we report a photochemical C–H annulation strategy for the direct synthesis of indanones from simple, unmodified aromatic aldehydes and terminal alkynes. The reaction proceeds under 365 nm light using tetrabutylphosphonium decatungstate ([Bu4P]4W10O32, TBPDT) as a hydrogen atom transfer (HAT) photocatalyst. This prefunctionalization-free protocol tolerates a broad range of substrates, eliminates the need for additional redox steps, and expands the toolbox for sustainable indanone synthesis.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.