桥环烯烃的 Rh 催化 C-H 键加成和酰胺化试剂的三组分 1,2-碳酰胺化反应。
Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via Rh-Catalyzed Addition of C-H Bonds and Amidating Reagents.
机构信息
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
出版信息
Org Lett. 2021 Apr 2;23(7):2836-2840. doi: 10.1021/acs.orglett.1c00851. Epub 2021 Mar 19.
Abstract
A three-component method is described for the preparation of -1,2-disubstituted bridged bicyclic compounds. The reaction was demonstrated for readily available aromatic and heteroaromatic C-H bond substrates with tertiary and secondary amide, lactam, pyrazole, and triazole directing groups and a variety of bridged bicyclic alkenes, including norbornene, benzonorbornadiene, oxygen- and nitrogen-bridged analogs, and an unsaturated tropinone. A broad dioxazolone scope was also observed. The use of a chiral Cp-derived Rh catalyst enables asymmetric synthesis of products.
摘要
本文描述了一种三组分方法，用于制备-1,2-二取代桥环双环化合物。该反应以易得的芳基和杂芳基 C-H 键底物为底物，具有叔酰胺、内酰胺、吡唑和三唑导向基团，以及各种桥环双环烯烃，包括降冰片烯、苯并降冰片二烯、氧桥和氮桥类似物，以及不饱和托品酮。还观察到宽范围的二恶唑酮。使用手性 Cp 衍生的 Rh 催化剂可实现产物的不对称合成。
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