Synthesis of Highly Functionalized 12-Membered Trifluoromethyl Heterocycles via a Nondecarboxylative Pd-Catalyzed [6 + 6] Annulation,ACS Catalysis

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Synthesis of Highly Functionalized 12-Membered Trifluoromethyl Heterocycles via a Nondecarboxylative Pd-Catalyzed [6 + 6] Annulation
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-01-07 , DOI: 10.1021/acscatal.9b05377
Hiroto Uno ₁ , Takanori Imai ₁ , Kyosuke Harada ₁ , Norio Shibata _{1,

2}

Affiliation

An efficient method for the construction of 12-membered heterocycles with a trifluoromethyl group (3) was achieved via a nondecarboxylative Pd-catalyzed [6 + 6] annulation of six-membered trifluoromethyl benzo[d][1,3]oxazinones (1) with four-membered vinyl oxetanes (2). A variety of relatively large heterocycles 3 featuring a stereogenic trifluoromethylated carbon center, an amino group, as well as an alkenyl and a carbonate moiety were obtained. An X-ray crystallographic analysis revealed a unique 3D architecture of the products that affords an attractive chemical space. Whereas the method can be applicable for nonfluorinated substrates, the trifluoromethyl group plays a vital role in this unexpected Pd-catalyzed nondecarboxylative ring expansion.

中文翻译：

通过非脱羧的Pd催化的[6 + 6]环合成高功能化的12元三氟甲基杂环

为12元与三氟甲基（杂环构造一个有效的方法3经由六元三氟甲基苯并[nondecarboxylative Pd催化[6 + 6]环达到）d ] [1,3] oxazinones（1）与四元乙烯基氧杂环丁烷（2）。各种相对较大的杂环3获得具有立体异构的三氟甲基化碳中心的特征，即氨基，烯基和碳酸酯部分。X射线晶体学分析揭示了该产品独特的3D结构，提供了诱人的化学空间。尽管该方法可用于非氟化底物，但是三氟甲基在这种意外的Pd催化的非脱羧环膨胀中起着至关重要的作用。

更新日期：2020-01-07

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