{"title":"异喹啉类化合物氮碳转化合成萘衍生物。","authors":"Tongtong Zhu, Xuhui Cui, Wenjun Ma, Xiujuan Qi, Hao Wei","doi":"10.1126/sciadv.ads5928","DOIUrl":null,"url":null,"abstract":"<div >Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges that can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations in isoquinolines, which is inspired by the Wittig reaction and enables easy access to substituted naphthalene derivatives. The reaction uses an inexpensive and commercially available phosphonium ylide as the carbon source to furnish a wide range of substituted naphthalenes. The key to the success of this transformation is the formation of a triene intermediate through ring opening, which undergoes 6π-electrocyclization and elimination processes to afford the naphthalene product. Furthermore, this strategy enables the facile synthesis of <sup>13</sup>C-labeled naphthalenes using <sup>13</sup>CH<sub>3</sub>PPh<sub>3</sub>I as a commercial <sup>13</sup>C source and facilitates modifying the directing group for C─H functionalization.</div>","PeriodicalId":21609,"journal":{"name":"Science Advances","volume":"11 5","pages":""},"PeriodicalIF":12.5000,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11777194/pdf/","citationCount":"0","resultStr":"{\"title\":\"Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines\",\"authors\":\"Tongtong Zhu, Xuhui Cui, Wenjun Ma, Xiujuan Qi, Hao Wei\",\"doi\":\"10.1126/sciadv.ads5928\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div >Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges that can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations in isoquinolines, which is inspired by the Wittig reaction and enables easy access to substituted naphthalene derivatives. The reaction uses an inexpensive and commercially available phosphonium ylide as the carbon source to furnish a wide range of substituted naphthalenes. The key to the success of this transformation is the formation of a triene intermediate through ring opening, which undergoes 6π-electrocyclization and elimination processes to afford the naphthalene product. Furthermore, this strategy enables the facile synthesis of <sup>13</sup>C-labeled naphthalenes using <sup>13</sup>CH<sub>3</sub>PPh<sub>3</sub>I as a commercial <sup>13</sup>C source and facilitates modifying the directing group for C─H functionalization.</div>\",\"PeriodicalId\":21609,\"journal\":{\"name\":\"Science Advances\",\"volume\":\"11 5\",\"pages\":\"\"},\"PeriodicalIF\":12.5000,\"publicationDate\":\"2025-01-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11777194/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Science Advances\",\"FirstCategoryId\":\"103\",\"ListUrlMain\":\"https://www.science.org/doi/10.1126/sciadv.ads5928\",\"RegionNum\":1,\"RegionCategory\":\"综合性期刊\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"MULTIDISCIPLINARY SCIENCES\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science Advances","FirstCategoryId":"103","ListUrlMain":"https://www.science.org/doi/10.1126/sciadv.ads5928","RegionNum":1,"RegionCategory":"综合性期刊","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"MULTIDISCIPLINARY SCIENCES","Score":null,"Total":0}
Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines
Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges that can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations in isoquinolines, which is inspired by the Wittig reaction and enables easy access to substituted naphthalene derivatives. The reaction uses an inexpensive and commercially available phosphonium ylide as the carbon source to furnish a wide range of substituted naphthalenes. The key to the success of this transformation is the formation of a triene intermediate through ring opening, which undergoes 6π-electrocyclization and elimination processes to afford the naphthalene product. Furthermore, this strategy enables the facile synthesis of 13C-labeled naphthalenes using 13CH3PPh3I as a commercial 13C source and facilitates modifying the directing group for C─H functionalization.
期刊介绍:
Science Advances, an open-access journal by AAAS, publishes impactful research in diverse scientific areas. It aims for fair, fast, and expert peer review, providing freely accessible research to readers. Led by distinguished scientists, the journal supports AAAS's mission by extending Science magazine's capacity to identify and promote significant advances. Evolving digital publishing technologies play a crucial role in advancing AAAS's global mission for science communication and benefitting humankind.