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A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins
Organic Letters ( IF 4.9 ) Pub Date : 2024-12-18 , DOI: 10.1021/acs.orglett.4c04260
Hannah C. Wendlandt, Jacob A. Utley, Byung Joo Lee, Tam D. Ho, Kami L. Hull

We disclose a broad platform for copper-catalyzed atom transfer radical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)2(OTf)2 enables radical addition of electron-deficient alkyl halides to acrylates, acrylamides, and vinyl sulfones in fair to excellent yields. The resultant ATRA products can be used in a variety of telescoped reactions, including substitution with basic amine nucleophiles to afford α-amino esters. The synthetic utility of the products is further demonstrated through derivatization to give substituted cyclopropanes and a γ,δ-unsaturated ester.

中文翻译:


铜催化的缺电子烯烃原子转移自由基加成的通用平台



我们公开了一个广泛的平台,用于缺电子烯烃的铜催化原子转移自由基加成 (ATRA)。催化 Cu(dtbbpy)2(OTf)2 能够以公平或优异的收率将缺电子烷基卤化物自由基添加到丙烯酸酯、丙烯酰胺和乙烯基砜中。所得 ATRA 产物可用于各种望远镜反应,包括用碱性胺亲核试剂取代以获得 α-氨基酯。通过衍生化得到取代的环丙烷和 γ,δ-不饱和酯,进一步证明了产品的合成效用。
更新日期:2024-12-19
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