Suzuki–Kumada coupling of bromoaroylmethylidenephosphoranes

Thiemann, Thies; Umeno, Kuniharu; Ohira, Daisuke; Inohae, Eiko; Sawada, Tsuyoshi; Mataka, Shuntarō

doi:10.1039/a907470h

Cited by 28 publications

(21 citation statements)

References 6 publications

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“…Although one of the most useful methods for aryl-aryl coupling is the Suzuki-Miyaura reaction, 17 the reaction between 3 and pentafluorophenylboronic acid with [Pd(PPh 3 ) 4 ], and K 2 CO 3 did not proceed. 18 Next, we examined the S N Ar reaction of the dianion from 3 toward HFB. 19 Thus, the dibromide 3 was treated with n-BuLi at À78 C in THF, and the resulting dianion was allowed to react with 20 equivalent of HFB; however, the desired product 1 was not obtained.…”

mentioning

confidence: 99%

Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent

Korenaga

Kawauchi

Kosaki

et al. 2005

Bulletin of the Chemical Society of Japan

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A molecular tweezer having two bidentate pentafluorophenyl (C 6 F 5 ) groups was synthesized, and the -stacking ability of the C 6 F 5 groups toward benzene derivatives in a polar organic solvent was evaluated. The structure of the molecular tweezer was revealed to be dimeric in the crystalline state by X-ray analysis. Association constants (K a ) between the molecular tweezer and aromatic guests in THF were found to be roughly correlated with the quadrupole moment (Q zz ) of the guests, suggesting that the quadrupole-quadrupole contribution plays a significant role in the -interaction even in a polar organic solvent.

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mentioning

confidence: 99%

Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent

Korenaga

Kawauchi

Kosaki

et al. 2005

Bulletin of the Chemical Society of Japan

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“…Often, the oxidant of choice is MnO 2 [40,[43][44][45][46][79][80][81][82][83][84][85][86][87][88][89][90][91][92][93][94][95][96][97], although a number of reactions are known where transformations were carried with air oxygen using metals and metal oxides as catalysts [72][73][74][75][76][77][78]. As many Wittig-and HWE reactions tolerate metal catalysts, this allows the running of Wittig/HWE reactions in combination with metal catalyzed cross coupling reactions and olefinations such as Heck [114][115][116][117][118][119][120][121][122][123], Suzuki [111][112][113], Sonogashira [119][120]…”

Section: Resultsmentioning

confidence: 99%

“…Initially, it was observed that conjugated phosphoranes were stable under reaction conditions used for Heck-or Suzuki reactions (Scheme 9). Thus, phosphoranes themselves could be functionalized by Suzuki- [120], Mizoroki-Heck- [121], or Sonogashira-type [119] cross-coupling reactions, either in solution or when polymer-bound [122]. These phosphoranes could then be subjected to normal Wittig-olefination reactions with ketones or aldehydes [120][121][122].…”

Section: Wittig-and Hwe Reactions and C─c-coupling Reactions In One-pmentioning

confidence: 99%

“…Thus, phosphoranes themselves could be functionalized by Suzuki- [120], Mizoroki-Heck- [121], or Sonogashira-type [119] cross-coupling reactions, either in solution or when polymer-bound [122]. These phosphoranes could then be subjected to normal Wittig-olefination reactions with ketones or aldehydes [120][121][122]. The one-pot Wittig-Heck-reaction strategy can be extended to include an O-alkylation, where the Wittig reaction of a p-hydroxybenzaldehyde (43) with methylenetriphenylphosphorane, obtained in situ from phosphonium salt 44 provides the p-hydroxystyrene as the olefin component in the Mizoroki-Heck reaction in the presence of an alkyl bromide (e.g., 45), which O-alkylates the phenoxy-function to give alkoxystilbenes 46 (Scheme 9) [123].…”

Section: Wittig-and Hwe Reactions and C─c-coupling Reactions In One-pmentioning

confidence: 99%

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Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Merza¹,

Taha²,

Thiemann³

2018

Alkenes

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The Wittig olefination utilizing phosphoranes and the related Horner-WadsworthEmmons (HWE) reaction using phosphonates transform aldehydes and ketones into substituted alkenes. Because of the versatility of the reactions and the compatibility of many functional groups towards the transformations, both Wittig olefination and HWE reactions are a mainstay in the arsenal of organic synthesis. Here, an overview is given on Wittig-and Horner-Wadsworth-Emmons (HWE) reactions run in combination with other transformations in one-pot procedures. The focus lies on one-pot oxidation Wittig/HWE protocols, Wittig/HWE olefinations run in concert with metal catalyzed cross-coupling reactions, Domino Wittig/HWE-cycloaddition and Wittig-Michael transformations.

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“…However, with the keto group in position at C6, C7 lends itself also to direct substitution by conjugate addition [63]. In this way, both carbon and heteroatomic nucleophiles can be added [64][65][66][67][68][69][70][71][72][73]. enolate in THF forms a dark, deep red solution.…”

Section: C) Direct Addition Of Substituents To C7 Of Estranesmentioning

confidence: 99%