利用光催化实现烯烃自由基阳离子与乙烯基重氮物种的环戊烯环化反应。
Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis.
作者信息
Sarabia Francisco J, Li Qiankun, Ferreira Eric M
机构信息
Department of Chemistry, University of Georgia, Athens, GA, 30602, USA.
出版信息
Angew Chem Int Ed Engl. 2018 Aug 20;57(34):11015-11019. doi: 10.1002/anie.201805732. Epub 2018 Jul 20.
Abstract
A direct (3+2) cycloaddition between alkenes and vinyl diazo reagents using either Cr or Ru photocatalysis is described. The intermediacy of a radical cation species enables a nucleophilic interception by vinyl diazo compounds, a departure from their traditional electrophilic behavior. A variety of cyclopentenes are synthesized using this method, and experimental insights implicate a direct cycloaddition instead of a cyclopropanation/rearrangement process.
摘要
描述了使用Cr或Ru光催化在烯烃和乙烯基重氮试剂之间进行直接的(3 + 2)环加成反应。自由基阳离子物种的中间体使得乙烯基重氮化合物能够进行亲核截获，这与其传统的亲电行为不同。使用该方法合成了多种环戊烯，实验结果表明这是一个直接的环加成反应，而非环丙烷化/重排过程。
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本文引用的文献
1
Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds.通过对重氮化合物的区分实现催化发散的[3+3]-和[3+2]-环加成反应。
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12292-12296. doi: 10.1002/anie.201706639. Epub 2017 Aug 24.
2
Cycloaddition reactions of enoldiazo compounds.烯醇重氮化合物的环加成反应。
Chem Soc Rev. 2017 Aug 29;46(17):5425-5443. doi: 10.1039/c7cs00324b.
3
Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis.通过铬光氧化催化的自由基阳离子环丙烷化反应。
Org Lett. 2017 Jun 2;19(11):2865-2868. doi: 10.1021/acs.orglett.7b01095. Epub 2017 May 12.
4
Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis.通过基于 Co(II)的金属自由基催化，通过原位生成供体取代重氮试剂实现烯烃的不对称自由基环丙烷化反应。
J Am Chem Soc. 2017 Jan 25;139(3):1049-1052. doi: 10.1021/jacs.6b11336. Epub 2017 Jan 12.
5
Recent Developments in Coinage Metal Catalyzed Transformations of Stabilized Vinyldiazo Compounds: Beyond Carbenic Pathways.稳定乙烯基重氮化合物的金属催化转化的最新进展：超越卡宾途径。
Chem Rec. 2017 Mar;17(3):312-325. doi: 10.1002/tcr.201600099. Epub 2016 Oct 4.
6
Highly Regio- and Enantioselective Formal [3 + 2]-Annulation of Indoles with Electrophilic Enol Carbene Intermediates.高区域和对映选择性的吲哚与亲电烯醇卡宾中间体的[3 + 2]-环加成反应。
Org Lett. 2016 Sep 16;18(18):4550-3. doi: 10.1021/acs.orglett.6b02192. Epub 2016 Sep 2.
7
Asymmetric Catalysis with Organic Azides and Diazo Compounds Initiated by Photoinduced Electron Transfer.光诱导电子转移引发的有机叠氮化物和重氮化合物的不对称催化反应。
J Am Chem Soc. 2016 Sep 28;138(38):12636-42. doi: 10.1021/jacs.6b07692. Epub 2016 Sep 14.
8
Catalytic Asymmetric Synthesis of Cyclopentyl β-Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates.通过烯碳酰胺与亲电金属烯醇卡宾中间体的[3+2]环加成反应催化不对称合成环戊基β-氨基酯。
Angew Chem Int Ed Engl. 2016 Aug 16;55(34):10108-12. doi: 10.1002/anie.201605438. Epub 2016 Jul 8.
9
Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes.金催化稳定化乙烯基重氮衍生物与电中性丙二烯的分子间形式上的（3+2）环加成反应。
Chem Commun (Camb). 2016 Jul 19;52(60):9398-401. doi: 10.1039/c6cc04106j.
10
Uncovering the Roles of Oxygen in Cr(III) Photoredox Catalysis.揭示氧在 Cr(III)光氧化还原催化中的作用。
J Am Chem Soc. 2016 Apr 27;138(16):5451-64. doi: 10.1021/jacs.6b02723. Epub 2016 Apr 15.
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