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Literature DB >> 26891077

Regio- and Stereoselective Cyanotriflation of Alkynes Using Aryl(cyano)iodonium Triflates.

Abstract

A novel, mild, and versatile approach for regioselective syn-addition of both the CN and OTf groups of aryl(cyano)iodonium triflates to alkynes is described. The reaction uses Fe-catalysis and can be conducted in gram scale. Products of the vicinal cyanotriflation can be stereospecifically readily further functionalized, rendering the method highly valuable.

Entities: Chemical Gene

Year: 2016 PMID： 26891077 DOI： 10.1021/jacs.6b00869

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

Authors: Beryl X Li; Diane N Le; Kyle A Mack; Andrew McClory; Ngiap-Kie Lim; Theresa Cravillion; Scott Savage; Chong Han; David B Collum; Haiming Zhang; Francis Gosselin
Journal: J Am Chem Soc Date: 2017-07-26 Impact factor: 15.419

2. Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation.

Authors: Jae Bin Lee; Gun Ha Kim; Ji Hwan Jeon; Seo Yeong Jeong; Soochan Lee; Jaehyun Park; Doyoung Lee; Youngkook Kwon; Jeong Kon Seo; Joong-Hyun Chun; Seok Ju Kang; Wonyoung Choe; Jan-Uwe Rohde; Sung You Hong
Journal: Nat Commun Date: 2022-05-03 Impact factor: 17.694

7. Synthesis of Fe^III and Fe^IV Cyanide Complexes Using Hypervalent Iodine Reagents as Cyano-Transfer One-Electron Oxidants.

Authors: Charafa Souilah; Sergio A V Jannuzzi; Derya Demirbas; Sergei Ivlev; Marcel Swart; Serena DeBeer; Alicia Casitas
Journal: Angew Chem Int Ed Engl Date: 2022-03-29 Impact factor: 16.823

8. Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.

Authors: Xi Wang; Armido Studer
Journal: Org Lett Date: 2017-05-18 Impact factor: 6.005

8 in total

Regio- and Stereoselective Cyanotriflation of Alkynes Using Aryl(cyano)iodonium Triflates.

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

2. Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation.

Review 3. Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

4. Iodine(III) Reagents in Radical Chemistry.

5. Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes.

6. Metal-Free Direct C-H Cyanation of Alkenes.

7. Synthesis of Fe^III and Fe^IV Cyanide Complexes Using Hypervalent Iodine Reagents as Cyano-Transfer One-Electron Oxidants.

8. Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.