Direct oxidative cyanation of tertiary amines promoted by in situ generated hypervalent iodine(III)-CN intermediate

Shen, Hang; Zhang, Xiaohui; Liu, Qing; Pan, Jing; Hu, Wen; Xiong, Yan; Zhu, Xiangming

doi:10.1016/j.tetlet.2015.08.058

Cited by 40 publications

(10 citation statements)

References 62 publications

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“…However, it often encounters selectivity issues, needs high catalyst loading, and is limited to Csp 2 carbons (using Rh, Co, Cu or Fe catalysts) 7 or weak Csp 3 –H bonds, especially α to heteroatoms (using metal catalysts, 8 or Hydrogen Atom Transfer (HAT)/oxidative methods). 9 …”

Section: Introductionmentioning

confidence: 99%

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

2017

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Section: Introductionmentioning

confidence: 99%

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

2017

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“…The formation of α‐cyanoamines 51 by oxidative cyanations of C―H bonds has been intensively studied in recent years . Several different protocols applying stoichiometric amounts of TMSCN under very mild (room temperature) and acid free conditions have been reported: (1) FeCl 2 , tert‐butyl hydroperoxide (TBHP), MeOH, rt (scheme ); (2) Au(bipyridyl)Cl 2 , 2 eq.…”

Section: Cyano‐group Sourcesmentioning

confidence: 99%

“…[36][37][38][39][40] Several different protocols applying stoichiometric amounts of TMSCN under very mild (room temperature) and acid free conditions have been reported: (1) FeCl 2 , tert-butyl hydroperoxide (TBHP), MeOH, rt (scheme 11) 36 ; (2) Au(bipyridyl)Cl 2 , 2 eq. TMSCN, TBHP, MeOH, rt (9 examples, 91%-98%) 37 ; (3) Oxorhenium-catalyst, TBHP, neat, rt 38 ; (4) PIFA, Na 2 SO 4 , DCE, 0°C 39 ; and (5) MoO 2 (acac) 2 , neat, O 2 , 80°C. 40 These methods are especially of interest as oxygen precursors of standard substitution reactions (eg, tosylates etc.)…”

Section: Trimethylsilylcyanide (Tmscn)mentioning

confidence: 99%

New trends and applications in cyanation isotope chemistry

Derdau

2018

Labelled Comp Radiopharmac

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In this review, newly developed cyanation methods are evaluated in regards to their usefulness in synthetic isotope chemistry. In combination with already established protocols in C- or C-isotope chemistry, this manuscript should help isotope scientists to choose the best possible method for their scientific cyanation problem, but with the main focus on C-applications. Perhaps, most promising of the described novel cyanation reaction is the decarboxylation-cyanation-hydrolysis approach which makes a 1-step late-stage functionalization procedure possible.

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“…[34,35] Towards the end of the 20 th century, metal and nonmetal catalyzed cyanation reactions were developed. [36] Transition metal catalysts like copper, [37][38][39] rhodium, [40,41] palladium, [42][43][44] iron, [45][46][47] and transition metal-free iodine-based CÀ H cyanation reactions [48][49][50] were rapidly explored. Despite the efficiency of these reactions, several drawbacks like the expensive nature, toxicity of metal catalyst have given way for the further developments in nitrile synthesis.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach

et al. 2022

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Nitriles unveil widespread applications in pharmaceuticals, agrochemicals, textiles, rubber, polymers, and constitute a significant intermediate in several organic transformations, necessitating the design of simple and environmentally benign pathways for their synthesis. Over the recent years, electro‐organic reactions have found widespread attention in developing effective and selective organic synthesis. They possess several advantages: high atom economy, selectivity, minimal waste production, and shorter routes to multistep traditional organic reactions. The development of novel strategies for greener and sustainable electro‐organic synthesis of nitriles is therefore commendable. This review focuses on analyzing various methods and strategies used in the electrochemical synthesis of nitriles using phase transfer catalyst, N‐oxoammonium salts mediated electrocatalysis, iodine‐mediated electrocatalysis, and anodic oxidations of aldoximes. In addition, the recent trends including the synthesis of nitriles via C−H cyanation, domino oxidation, bio electrocatalysis, and metal‐ligand cooperative synthesis have been discussed.

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Direct oxidative cyanation of tertiary amines promoted by in situ generated hypervalent iodine(III)-CN intermediate

Cited by 40 publications

References 62 publications

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

New trends and applications in cyanation isotope chemistry

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach

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