Reaction of Diazonium Salts With Transition Metals. I. Arylation of Olefins With Arenediazonium Salts Catalyzed by Zero Valent Palladium

Kikukawa, Kiyoshi; Matsuda, Tsutomu

doi:10.1246/cl.1977.159

Cited by 205 publications

(138 citation statements)

References 11 publications

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“…A review by Oestreich [46] summarizes the exciting development of the enantioselective intermolecular Heck reaction (particularly the Heck-Matsuda [47] reaction that uses arene diazonium salts as an alternative to aryl halides and triflates) of acyclic alkenes and the synthetic utility of enantioselective intermolecular couplings of cyclic alkenes. Many such examples that give very high enantioselectivity for intermolecular Heck reactions are cited.…”

Section: Intramolecular Heck Reactionmentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

173

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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Section: Intramolecular Heck Reactionmentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

173

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“…Various solvents were used for palladium-mediated coupling reactions of diazonium salts with electrondeficient olefins, such as alcohols, [47] [ 48] water, [49] acetoScheme 5. Pd-mediated coupling of p-tolyldiazonium trifluoroacenitrile, [12] [50] CH 2 Cl 2 /acetone, [51] and dioxane. [13] Table 5 tate with ethyl acrylate (see Table 5) shows the results we obtained on testing ethanol, acetonitrile, dichloromethane, and dioxane in coupling reactions cation reactions.…”

Section: Quinone Diazidesmentioning

confidence: 99%

“…[12] This reaction has been extended to many other substrates (see ref. [13] and references cited therein) and has attracted great interest by virtue of its mildness and simplicity.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

Colas

Goeldner²

1999

Eur. J. Org. Chem.

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We have developed a very mild procedure for the synthesis of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono‐ or polyfunctional aniline derivatives have been diazotized by this method, including water‐ and acid‐sensitive substrates. The o‐ and p‐hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment with K2CO3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C‐NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants s+p and the 13Cipso chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents than their tetrafluoroborate counterparts. They were tested in Pd‐mediated coupling reactions of various Carbon‐Carbon double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates.

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“…1 There are very few reports describing this enantioselective reaction. 2,3 Because of the great interest in the synthesis of chiral compounds, new enantioselective methods are welcome.…”

Section: Introductionmentioning

confidence: 99%

Studies on the enantioselective Heck arylation of Ncarboethoxy 3-pyrroline with aryldiazonium salts

Lustosa¹,

Correia

2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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Reaction of Diazonium Salts With Transition Metals. I. Arylation of Olefins With Arenediazonium Salts Catalyzed by Zero Valent Palladium

Abstract: Various olefins, especially those bearing electron donating groups, were successfully arylated by arenediazonium salts in the presence of a catalytic amount of palladium(O) complexes. An arylpalladium species was supposed to be an intermediate in this reaction.

Cited by 205 publications

References 11 publications

Heck Reaction—State of the Art

Heck Reaction—State of the Art

An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

Studies on the enantioselective Heck arylation of Ncarboethoxy 3-pyrroline with aryldiazonium salts

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