Palladium−Tetraphosphine as Catalyst Precursor for High-Turnover-Number Negishi Cross-Coupling of Alkyl- or Phenylzinc Derivatives with Aryl Bromides

Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice

doi:10.1021/om060605p

Cited by 59 publications

(21 citation statements)

References 46 publications

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“…The biaryl structural skeleton has a unique feature in many pharmaceutically relevant and biologically active molecules [1]. There is a broad spectrum of protocols available for the construction of aryl-aryl bonds through the usage of transition metal-catalysed reactions [2]. The earlier reports focused on the use of stoichiometric proportions of transition metal to precede the desired transformations.…”

Section: Introductionmentioning

confidence: 99%

Synthetic journey towards transition metal-free arylations

Roopan

Palaniraja

2014

Res Chem Intermed

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In general, aryl-aryl transformations were investigated via transition metal-catalysed reactions. However, transition metal-mediated organic synthesis provided higher yields but has some flaws such as high cost, and the need for careful exclusion of air and moisture during the reactions. Possibly, there may be contamination of the product from traces of heavy metals present. To overcome these kinds of disadvantages, continuous efforts have been focused on the recent development of aryl-aryl formation through transition metal-free (TMF) reactions. However, most of these cross-couplings reaction were limited to hetero and electron-rich arenes which require strong inorganic bases. Our critical review includes a synthetic pathway to prepared X-aryl (X = C, N, O and S) motif by a transition metal-free scenario. Formerly, TMF reactions were carried out by various sources like strong bases, diazodium salt, aryliodonium salt, organo-catalysts and versatile energy sources like microwave heating, visible light and photochemical reactor. In this review, we have focused on the transition metal-free arylations.

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Section: Introductionmentioning

confidence: 99%

Synthetic journey towards transition metal-free arylations

Roopan

Palaniraja

2014

Res Chem Intermed

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“…A similar observation with Tedicyp/Pd as catalyst has recently been described. [63] With this catalytic system the coupling of sec-butylzinc bromide with electron-excessive or -deficient aryl bromides gave the sec-butylarenes in good yields in most cases. Under similar reaction conditions, the coupling of s-butylboronic acid with aryl halides did not proceed.…”

Section: Alkylations Of Aryl Halides With Secondary Alkylboronic Acidmentioning

confidence: 94%

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

2008

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Palladium‐catalysed Suzuki–Miyaura cross‐couplings of organoboronic acids or organotrifluoroborates with aryl and alkenyl halides or triflates have become classic methods for generating carbon–carbon bonds. For this reaction, not only sp2‐hybridized but also sp3‐hybridized organoboron derivatives can be employed. However, alkylboronic acids or trifluoroborates are generally less reactive than arylboron derivatives. The coupling of primary alkylboronic acids or alkyltrifluoroborates with aryl or alkenyl halides is well known, and the reaction gives the coupling products with high selectivities, relatively high turnover numbers and in good yields with several catalysts. On the other hand, secondary alkylboronic acids or trifluoroborates, except for cyclopropylboron derivatives, are much less reactive, and very few catalyst are able to activate such compounds. Because of the hybridization of cyclopropanes, which confers significant aromatic character, several reactions have successfully been performed with cyclopropylboronic acids or trifluoroborates. The stereochemistries of substituted cyclopropylboron derivatives were maintained in the course of the reactions. For all these couplings with primary or secondary alkylboron derivatives, aryl iodides, bromides, chlorides or triflates and alkenyl iodides, bromides or triflates were employed. Alkenyl chlorides have attracted less attention. The reactions with alkenyl halides are stereoselective. A few examples of couplings between sp3‐hybridized organoboronic acids and alkyl halides have also been reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…Furthermore, homobimetallic dimers derived from phosphinous acids [134] or phosphine chlorides [239], palladium nanoparticles stabilized by nBu 4 NBr [142], as well as the catalyst derived from [Pd(C 3 H 5 )Cl] 2 as well as the tetraphosphine ligand Tedicyp (1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane) [240] are also systems with high catalytic activity that enable the cross-coupling of primary alkylzincs and aryl bromides or iodides with good generality.…”

Section: Cross-coupling With C(sp)-and C(sp 2 )-Electrophilesmentioning

confidence: 99%