Difluoroisoxazolacetophenone: A Difluoroalkylation Reagent for Organocatalytic Vinylogous Nitroaldol Reactions of 1,2-Diketones.
Difluoroisoxazolacetophenone: A Difluoroalkylation Reagent for Organocatalytic Vinylogous Nitroaldol Reactions of 1,2-Diketones.
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DOI：
10.1021/acs.orglett.0c02873
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发表时间：
2020-09
期刊：
影响因子：
5.2
通讯作者：
Yong Zhang;Jin Ge;Liang Luo;Su-Qiong Yan;Guo-Wei Lai;Zu-Qin Mei;Hairong Luo;Xiao-Lin Fan
中科院分区：
文献类型：
--
作者：
Yong Zhang;Jin Ge;Liang Luo;Su-Qiong Yan;Guo-Wei Lai;Zu-Qin Mei;Hairong Luo;Xiao-Lin Fan
二氟异恶唑苯乙酮（DFIO）是一种新型的二氟烷基化试剂，可以从廉价的起始原料容易地制备。DFIO的原位远程C-C键断裂得到γ，γ-二氟异恶唑硝酸酯，其经历碱催化的乙烯基硝基醛醇加成到靛红、苯并噻托烷-2，3-二酮、不饱和-α-酮酯和环状1，2-二酮。该反应为制备各种二氟异恶唑取代的3-羟基-2-羟吲哚提供了一种新的温和的方法。
Difluoroisoxazolacetophenone (DFIO) is developed as a new difluoroalkylation reagent that can be easily prepared from inexpensive starting materials. In situ remote C-C bond cleavage of DFIO affords γ,γ-difluoroisoxazole nitronate that undergoes base-catalyzed vinylogous nitroaldol additions to isatins, benzothiophene-2,3-dione, unsaturated-α-ketoesters, and cyclic 1,2-diketones. This organocatalytic debenzoate vinylogous nitroaldol reaction provides a new and mild approach for the preparation of various difluoroisoxazole-substituted 3-hydroxy-2-oxindoles.