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Organic Photoredox Catalysis for Pschorr Reaction: A Metal-Free and Mild Approach to 6H-Benzo[c]chromenes
Synlett ( IF 1.7 ) Pub Date : 2018-09-12 , DOI: 10.1055/s-0037-1610279
Gaofeng Feng 1 , Jing-Yao He , Qi-Fan Bai , Chengan Jin
Affiliation  

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6 H -benzo[ c ]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed or generated in situ from the corresponding amines with t -BuONO. The process is amenable to gram-sale synthesis of 6 H -benzo[ c ]chromenes, which can be further transformed into both 6 H -benzo[ c ]chromen-6-ones through oxidation or to 6 H -benzo[ c ]chromen-6-amine through sp 3 C–H bond amination. The protocol provides an attractive route for the synthesis of a library of 6 H -benzo[ c ]chromes.

中文翻译:

用于 Pschorr 反应的有机光氧化还原催化:一种无金属且温和的 6H-苯并 [c] 色烯方法

已开发出一种方便的有机光氧化还原 Pschorr 反应,为 6 H-苯并 [c] 色烯开辟了一条合成路线。该过程可以在温和的条件下通过使用曙红Y作为光氧化还原催化剂和乙腈作为溶剂进行。重氮盐可以由相应的胺与 t-BuONO 预先形成或原位生成。该工艺适用于6 H-苯并[ c ]色烯的克销售合成,其可以通过氧化进一步转化为6 H-苯并[ c ]色烯-6-酮或6 H-苯并[ c ]色烯-6-胺通过 sp 3 C-H 键胺化。该协议为合成 6 H-苯并 [c] 铬库提供了一条有吸引力的途径。
更新日期:2018-09-12
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