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Difluorocarbene Enables Modular Synthesis of Difluoroalkylated Bicyclopentanes
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-30 , DOI: 10.1002/ejoc.202400572 Meng-Die Zhang 1 , Hai-Yang Zhao 2 , Xingang Zhang 3
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-30 , DOI: 10.1002/ejoc.202400572 Meng-Die Zhang 1 , Hai-Yang Zhao 2 , Xingang Zhang 3
Affiliation
A straightforward method for the synthesis of difluoroalkylated bicyclopentanes (BCPs) from [1.1.1]propellane (TCP) through a stepwise procedure has been developed. This process involves nucleophilic addition of organozinc or ArMgBr rea-gents to TCP, followed by reaction with difluorocarbene to generate BCP substituted difluoroalkylzinc species, which subsequently couple with electrophiles, including allyl/propargyl bromides, (hetero)aryl disulfides, and proton, to provide a wide range of difluoroalkylated BCPs that otherwise are difficult to access through conventional methods. The transformations of the resulting products demonstrate the synthetic utility of this modular synthesis.
中文翻译:
二氟卡宾能够模块化合成二氟烷基化双环戊烷
已经开发出一种通过分步程序从[1.1.1]丙烷(TCP)合成二氟烷基化双环戊烷(BCP)的简单方法。该过程涉及将有机锌或 ArMgBr 试剂亲核加成到 TCP 上,然后与二氟卡宾反应生成 BCP 取代的二氟烷基锌物质,随后与亲电试剂(包括烯丙基/炔丙基溴、(杂)芳基二硫化物和质子)偶联,提供多种二氟烷基化 BCP,否则很难通过传统方法获得。所得产品的转化证明了这种模块化合成的综合效用。
更新日期:2024-07-01
中文翻译:
![](https://static.x-mol.com/jcss/images/paperTranslation.png)
二氟卡宾能够模块化合成二氟烷基化双环戊烷
已经开发出一种通过分步程序从[1.1.1]丙烷(TCP)合成二氟烷基化双环戊烷(BCP)的简单方法。该过程涉及将有机锌或 ArMgBr 试剂亲核加成到 TCP 上,然后与二氟卡宾反应生成 BCP 取代的二氟烷基锌物质,随后与亲电试剂(包括烯丙基/炔丙基溴、(杂)芳基二硫化物和质子)偶联,提供多种二氟烷基化 BCP,否则很难通过传统方法获得。所得产品的转化证明了这种模块化合成的综合效用。