Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles.,Organic Letters

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Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles.
Organic Letters ( IF 4.9 ) Pub Date : 2020-08-05 , DOI: 10.1021/acs.orglett.0c02138
Ekta Nag ₁ , Sai Manoj N V T Gorantla ₂ , Selvakumar Arumugam ₂ , Aditya Kulkarni ₁ , Kartik Chandra Mondal ₂ , Sudipta Roy ₁

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A Schiff-base nickel(II)-phosphene-catalyzed chemodivergent C–H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.

中文翻译：

三齿镍（II）催化的化学发散CH功能化和环丙烷化：取代芳香杂环的区域选择性和非对映选择性。

据报道，席夫碱镍（II）-膦催化的化学发散C–H官能团和芳族杂环的环丙烷化具有中等至极好的收率，以及非常好的区域选择性和非对映选择性。ligand配体与Ni中心之间的弱，非共价相互作用促进了配体的离解，从而生成了电子和配位不饱和活性催化剂。所报导的反应机理与实验结果和理论计算结果吻合良好，为环丙烷化反应提供了合适的立体控制模型。

更新日期：2020-08-21

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