4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents:  Experimental and Computational Studies

Neuville, Luc; Bigot, Antony; Dau, Marie Elise Tran Huu; Zhu, Jieping

doi:10.1021/jo990559l

Cited by 36 publications

(29 citation statements)

References 34 publications

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“…Besides NfF recently an alternative nonaflyl transfer reagent has been reported: the group of Zhu found that (like 4‐nitrophenyl triflate) 4‐nitrophenyl nonaflate acts as potent perfluoroalkanesulfonyl transfer agent, providing a number of aryl nonaflates in good to excellent yields 88. This group included theoretical calculations on the mechanism of the sulfonylation reaction.…”

Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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How much fluoride is good for a strong electron-withdrawing effect? In this review we summarize recent results on the use of perfluoroalkanesulfonates, in particular of the cost effective nonafluorobutanesulfonates (nonaflates), in transition metal-catalyzed reactions and a few other typical transformations. During the last decade many advantages over the commonly used triflates have been discovered. The generation of alkenyl and (het)aryl nonaflates and their applications in metal-catalyzed processes such as Heck, Suzuki, Sonogashira, Stille, and Negishi couplings or amination reactions are described. Although far from a systematic investigation, all the presented results clearly demonstrate the many advantages of nonaflates and of similar higher fluorinated sulfonates in laboratory and industrial scale organic synthesis.

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Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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“…To the best of our knowledge, the Mizoroki-Heck reaction of an aryl fluoroalkylsulfonate with trimethylvinylsilane is unprecedented and this example represented an even more daunting challenge because of the ortho-substituent on aryl triflate 15 63. The initial survey employed the phosphine-free “Jeffrey conditions”64 (Table 4, entry 1).…”

Section: Resultsmentioning

confidence: 99%

Development of a General, Sequential, Ring-Closing Metathesis/Intramolecular Cross-Coupling Reaction for the Synthesis of Polyunsaturated Macrolactones

Denmark

Muhuhi

2010

J. Am. Chem. Soc.

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A general strategy for the construction of macrocyclic lactones containing conjugated Z,Z-1,3-diene subunits has been is described. The centerpiece of the strategy is a sequential ring-closing metathesis that forms an unsaturated siloxane ring followed by an intramolecular cross-coupling reaction with a pendant alkenyl iodide. A highly modular assembly of the various precursors allowed the preparation of unsaturated macrolactones containing 11-, 12-, 13-and 14-membered rings. Although the ring closing metathesis process proceeded uneventfully, the intramolecular cross-coupling required extensive optimization of palladium source, solvent, fluoride source and particularly fluoride hydration level. Under the optimal conditions (including syringe pump high dilution), the macrolactones were produced in 53-78% yield as single stereoisomers. A benzo fused 12-membered ring macrolactone containing an E,Z-1,3-diene unit was also prepared by the same general strategy. The E-2-styryl iodide was prepared by a novel Heck reaction of an aryl nonaflate with vinyltrimethylsilane followed by iododesilylation with ICl.

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“…It should be noted that S N Ar reactions of aryl fluorides generally proceed readily with electron-rich phenols and sluggishly with electron-poor phenols. To our surprise, using CsF/CP, even phenols bearing an electron-withdrawing group such as nitro and cyano could also serve as efficient coupling partners ( [21][22][23][24][25]. However, this protocol provided good yields only for electron-deficient aryl fluorides, chlorides and bromides.…”

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confidence: 99%

CsF/clinoptilolite: an efficient solid base in S_NAr and copper-catalyzed Ullmann reactions

et al. 2016

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CsF/Clinoptilolite (CsF/CP) was found to be an efficient solid base catalyst for both S N Ar and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/CP. The protocol was also applied to electronrich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both S N Ar and Ullmann reactions were rapid and provided good to excellent yields.

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4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents: Experimental and Computational Studies

Cited by 36 publications

References 34 publications

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Development of a General, Sequential, Ring-Closing Metathesis/Intramolecular Cross-Coupling Reaction for the Synthesis of Polyunsaturated Macrolactones

CsF/clinoptilolite: an efficient solid base in S_NAr and copper-catalyzed Ullmann reactions

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4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents: Experimental and Computational Studies

Cited by 36 publications

References 34 publications

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Development of a General, Sequential, Ring-Closing Metathesis/Intramolecular Cross-Coupling Reaction for the Synthesis of Polyunsaturated Macrolactones

CsF/clinoptilolite: an efficient solid base in SNAr and copper-catalyzed Ullmann reactions

Contact Info

Product

Resources

About

CsF/clinoptilolite: an efficient solid base in S_NAr and copper-catalyzed Ullmann reactions