Gold‐Catalyzed Suzuki Coupling of <i>ortho</i>‐Substituted Hindered Aryl Substrates

Dwadnia, Nejib; Roger, Julien; Pirio, Nadine; Cattey, Hélène; Salem, Ridha Ben; Hierso, Jean‐Cyrille

doi:10.1002/asia.201601583

Cited by 29 publications

(17 citation statements)

References 27 publications

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“…The potential of (P,N) Au(I) complexes in Au(I)/Au(III) catalysis is also demonstrated by the development of arylation reactions involving aryl halides and catalyzed by well-defined mononuclear gold complexes. Precedents of gold-catalyzed cross-coupling reactions with aryl halides are extremely rare 49 – 51 , and involve polynuclear species.…”

Section: Introductionmentioning

confidence: 99%

Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides

Zeineddine¹,

Estévez²,

et al. 2017

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The reluctance of gold to achieve oxidative addition reaction is considered as an intrinsic limitation for the development of gold-catalyzed cross-coupling reactions with simple and ubiquitous aryl halide electrophiles. Here, we report the rational construction of a Au(I)/Au(III) catalytic cycle involving a sequence of Csp2–X oxidative addition, Csp2–H auration and reductive elimination, allowing a gold-catalyzed direct arylation of arenes with aryl halides. Key to this discovery is the use of Me-Dalphos, a simple ancillary (P,N) ligand, that allows the bottleneck oxidative addition of aryl iodides and bromides to readily proceed under mild conditions. The hemilabile character of the amino group plays a crucial role in this transformation, as substantiated by density functional theory calculations.

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Section: Introductionmentioning

confidence: 99%

Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides

Zeineddine¹,

Estévez²,

et al. 2017

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“…FT‐IR analyses of these complexes revealed the expected absorption bands between 321 cm –1 and 333 cm –1 and the XRD structure of [72–Au 2 Cl 2 ] confirmed a dinuclear gold(I) chloride linear coordination involving exclusively –P( i‐ Pr) 2 groups. For the ligand 71 , one equivalent of gold precursor was used in an attempt to obtain a mononuclear complex, but this reaction only led to a 1:1 mixture of the dinuclear complex together with the uncoordinated diaminodiphosphino ferrocene …”

Section: Ferrocenyl Amines and (P N)‐hybridsmentioning

confidence: 99%

Highly Functionalized Ferrocenes

et al. 2020

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Ferrocene is unique among organometallic compounds, and serves notably as a versatile platform towards the production of ligands useful to promote transition metals chemistry. A general limiting aspect of the synthesis of ferrocene derivatives is the efficient access to sophisticated highly functionalized polysubstituted ferrocenes, i.e. bearing four or more substituents replacing hydrogen atoms on the cyclopentadienyl rings. These ferrocene derivatives can bear various functional or/and structuring spectator substituents. Their preparation involves synthetic difficulties resulting from the need of multiple functionalizations coexisting altogether, and satisfying functional group compatibility and high selectivity issues. In the last decades, our group initially designed highly functionalized polyphosphines and hybrid ligands (1,1′,3,3′-tetrafunctionalized

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“…40,41 It is important to note that there are several gold catalyzed methodologies disclosed in the literature for cross-coupling reactions and are either limited to Sonogashira [38][39][40][41][42][43][44][45] or Suzuki. [46][47][48][49] Our approach differs from these protocols with an objective of establishing a generalized protocol that can accommodate an array of substrates suitable for both Suzuki as well as Sonogashira coupling. Towards this end, we initiated our studies by reuxing a mixture of iodobenzene (0.01 mol), phenylboronic acid (0.01 mol), NaOH (0.02 mol) and AuNPs (0.5 mol%) in water for 1 h (Table 1).…”

Section: Catalytic Tests Towards Cross-coupling Reactionsmentioning

confidence: 99%

“…Differing from previous gold catalysis disclosures on these reactions ( Fig. 1), our working hypothesis comprises a generalized procedure that could accommodate both Sonogashira [38][39][40][41][42][43][44][45] as well as Suzuki [46][47][48][49] reactions. Keeping in mind the principles of green chemistry, our focus is also to execute the abovementioned transformations in aqueous media.…”

Section: Introductionmentioning

confidence: 99%