Palladium catalyzed cross- and homo-coupling reactions of 4-Halo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes with various organometallic reagents

Roche, Alex J.

doi:10.1016/j.jfluchem.2015.02.016

Cited by 3 publications

(2 citation statements)

References 32 publications

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“…For almost 40 years now, palladium‐catalyzed cross‐coupling reactions represent a powerful tool in organic synthesis for the formation of new CC bonds. Brominated [2.2]paracyclophanes 1a‐Br 5 and 1c‐Br 6 are very well investigated in Suzuki couplings,7 Stille couplings,8 Heck reactions,7c,9 and Kumada reactions 10. Suzuki couplings of the corresponding triflate,7j,11 Kumada coupling of paracyclophanyl‐Grignard reagents12 and reactions of paracyclophanyl‐palladium complexes have also been reported 13.…”

Section: Introductionmentioning

confidence: 99%

Efficient Modular Synthesis of Isomeric Mono‐ and Bispyridyl[2.2]paracyclophanes by Palladium‐Catalyzed Cross‐ Coupling Reactions

et al. 2016

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Pyridyl-substituted [2.2]paracyclophanes build am ultifunctional structural motif that is useful in material chemistry,c atalysis and for luminescent structures.N onetheless,t here is still al ack of general methodsf or the synthesiso ft hese structures tolerating easily accessiblebromides as well as different isomeric pyridyl groups.H ence the coupling of functionalized [2.2]paracyclophanes with various substituted andf unctionalized pyridyl derivatives was ach-ieved using Stille,S uzuki andK umada coupling conditions.H ereby the Stille coupling of a [2.2]paracyclophane is presenteda saversatile reaction for the formation of heteromeric [2.2]paracyclophane-containing biaryl structures.

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Section: Introductionmentioning

confidence: 99%

Efficient Modular Synthesis of Isomeric Mono‐ and Bispyridyl[2.2]paracyclophanes by Palladium‐Catalyzed Cross‐ Coupling Reactions

et al. 2016

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“…First, we had a general desire to improve the efficiency and yield of this reaction. Second, given the recently reported propensity of PhMgBr to promote homocouplings in related systems, 20 we were curious to see whether this method could similarly produce tris(OFP) or larger poly(OFP)-type molecules starting from difunctional 5.…”

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confidence: 99%

The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene

Roche

Abboud

2015

J. Org. Chem.

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An investigation of the palladium-catalyzed Kumada cross-coupling reaction between PhMgBr and (pseudo-ortho) 4,12-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane revealed that in addition to the expected cross-coupled product, an unintended major product was generated. The product was determined to be 9,9,10,10-tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene by X-ray crystallography and is proposed to be formed via the first reported example of reductive defluorination by a Grignard reagent.

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Advances in Kumada–Tamao–Corriu cross-coupling reaction: an update

et al. 2019

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The formation of the CC bond is a major and important reaction in synthetic organic chemistry and frequently catalyzed by transition-metal catalysts. Among them, Kumada-Tamao-Corriu coupling reaction is providing a simple methodology and extensively employed in the art of organic synthesis. In this review, we try to highlight the recent advances in the applications of Kumada-Tamao-Corriu coupling reaction by updating of our previous review from 2012 up to date.

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Palladium catalyzed cross- and homo-coupling reactions of 4-Halo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes with various organometallic reagents

Cited by 3 publications

References 32 publications

Efficient Modular Synthesis of Isomeric Mono‐ and Bispyridyl[2.2]paracyclophanes by Palladium‐Catalyzed Cross‐ Coupling Reactions

Efficient Modular Synthesis of Isomeric Mono‐ and Bispyridyl[2.2]paracyclophanes by Palladium‐Catalyzed Cross‐ Coupling Reactions

The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene

Advances in Kumada–Tamao–Corriu cross-coupling reaction: an update

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