A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters 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
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Abstract

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.

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铜催化原子转移自由基加成与缺电子烯烃的通用平台
我们揭示了一个广泛的平台铜催化原子转移自由基加成(ATRA)的缺电子烯烃。催化Cu(dtbbpy)2(OTf)2能使缺乏电子的烷基卤化物自由基加成到丙烯酸酯、丙烯酰胺和乙烯基砜,收率相当高。所得的ATRA产物可用于多种缩合反应,包括与碱性胺亲核试剂取代生成α-氨基酯。通过衍生得到取代环丙烷和γ,δ-不饱和酯,进一步证明了该产物的合成用途。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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