{"title":"Dearomative Addition of Carboranyl Anions to Isoquinolinium Salts and Subsequent Reduction to Access Carborane‐Functionalized Dihydroisoquinolines","authors":"Yun-Fan Gao, Chen-Ming Xu, Ming-Hui Yu, Yongna Zhang, Xiao-Jun Wu, You-Qing Wang","doi":"10.1002/ajoc.202400390","DOIUrl":null,"url":null,"abstract":"A dearomative addition of readily available carboranyllithium reagents to isoquinolinium salts gave a series of carborane cage C‐substituted 1,2‐dihydroisoquinolines in 43−85% yields. Subsequent hydrogenation enabled the facile synthesis of corresponding carboranyl 1,2,3,4‐tetrahydroisoquinolines in 65−95% yields. The addition‐reduction pathway is applicable to a wide range of substituted isoquinolinium salts and o‐carborane or m‐carborane.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.8000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ajoc.202400390","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
A dearomative addition of readily available carboranyllithium reagents to isoquinolinium salts gave a series of carborane cage C‐substituted 1,2‐dihydroisoquinolines in 43−85% yields. Subsequent hydrogenation enabled the facile synthesis of corresponding carboranyl 1,2,3,4‐tetrahydroisoquinolines in 65−95% yields. The addition‐reduction pathway is applicable to a wide range of substituted isoquinolinium salts and o‐carborane or m‐carborane.
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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