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Brønsted Acid Catalyzed Dehydroxylative Cyanation of Benzylic Alcohols with Trimethylsilyl Cyanide Using 1,1,1,3,3,3‐Hexafluoro‐2‐propanol as a Solvent
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-05-07 , DOI: 10.1002/ejoc.202400474
Kosho Makino 1 , Mai Hasebe 2 , Shunsuke Sueki 3 , Masahiro Anada 4
Affiliation  

A concise and direct cyanation of secondary and tertiary benzylic and allylic alcohols catalyzed by Brønsted acid has been developed using trimethylsilyl cyanide (TMSCN) as a cyanide source and 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) as a solvent. The present transition metal‐free catalytic process is operationally simple to perform under “open‐flask” conditions and it is applicable to the preparation of a number of α‐arylacetonitriles as well as late‐stage material transformations. The effectiveness of the present protocol was further demonstrated by the first enantioselective synthesis and determination of the absolute configuration of verimol F.

中文翻译:

布朗斯台德酸催化苯甲醇与三甲基氰硅烷以 1,1,1,3,3,3-六氟-2-丙醇为溶剂进行脱羟基氰化

使用三甲基硅烷基氰(TMSCN)作为氰化物源和 1,1,1,3,3,3-六氟-2-丙醇(HFIP )作为溶剂。目前的无过渡金属催化工艺在“开瓶”条件下操作简单,适用于多种α-芳基乙腈的制备以及后期材料转化。通过首次对映选择性合成和 verimol F 绝对构型的测定,进一步证明了本方案的有效性。
更新日期:2024-05-07
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