Gold-Catalyzed 1,2-Aminoarylation of Alkenes with External Amines

Tathe, Akash G.; Urvashi, .; Yadav, Amit Kumar; Chintawar, Chetan C.; Patil, Nitin T.

doi:10.1021/acscatal.1c00789

Cited by 64 publications

(30 citation statements)

References 84 publications

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“…In the case of oxyarylations, two‐ and three‐component reactions were reported, whereas aminoarylations were only carried out as two‐component reactions. The 1,2‐aminoarylations of alkenes were also shown to proceed by reacting alkenes tethered to aryl iodide moieties with external amines [74] . The use of MeDalphos ligand allowed the same group to develop, as well, the first ligand‐enabled Au(I)/Au(III)‐catalyzed 1,2‐diarylation of alkenes by merging the oxidative addition of aryl iodides to Au(I) with π‐activation of alkenes (Figure 13e) [75] .…”

Section: Oxidant‐free Au(i)/au(iii) Cross‐coupling Catalysismentioning

confidence: 99%

“…The 1,2aminoarylations of alkenes were also shown to proceed by reacting alkenes tethered to aryl iodide moieties with external amines. [74] The use of MeDalphos ligand allowed the same group to develop, as well, the first ligand-enabled Au(I)/Au(III)catalyzed 1,2-diarylation of alkenes by merging the oxidative addition of aryl iodides to Au(I) with π-activation of alkenes (Figure 13e). [75] In this case, the mechanism was proposed to involve an aromatic electrophilic substitution (S E Ar) step for the carboauration of alkenes.…”

Section: Substrate and Ligand Design For The Development Of Au(i)/au(iii) Catalytic Cyclesmentioning

confidence: 99%

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Fundamental Basis for Implementing Oxidant‐Free Au(I)/Au(III) Catalysis

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2021

Eur J Inorg Chem

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Oxidant-free Au(I)/Au(III) catalysis can still be regarded as a young and promising chemistry. Because the first examples of gold catalysis were limited to the activation and functionalization of π-CÀ C bonds and very little was known on fundamental organometallic transformations at gold, countless works during the past 15 years have been devoted to disclosing the elementary reactivity of gold and implementing it in catalysis. Remarkably, great emphasis on triggering oxidative addition at Au(I) has been placed, as the high redox potential of the Au(I)/ Au(III) pair disfavors this reaction. In fact, different strategies such as strain release, ligand design and photochemistry have been proven successful at allowing the bottleneck oxidative addition to occur. These approaches have led to the rational development of oxidant-free Au(I)/Au(III) redox catalysis, particularly catalytic cycles in cross-coupling transformations where oxidative addition is usually the entry point to the cycle. Herein, the background story, the development process, and relevant examples of oxidant-free gold-catalyzed cross-coupling reactions are reviewed.

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Section: Oxidant‐free Au(i)/au(iii) Cross‐coupling Catalysismentioning

confidence: 99%

Section: Substrate and Ligand Design For The Development Of Au(i)/au(iii) Catalytic Cyclesmentioning

confidence: 99%

Fundamental Basis for Implementing Oxidant‐Free Au(I)/Au(III) Catalysis

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Ribas

2021

Eur J Inorg Chem

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“…[12] However, the high redox potential of Au(I)/Au(III) couple [54] [E 0 = 1.43 eV] compared to Pd(0)/Pd(II) couple [E 0 = 0.91 eV] renders the oxidative addition pathway extremely difficult for gold-catalyzed processes. Although, the recent literature enjoyed the feasibility of oxidative addition of CÀ X (X=I or Br) bond at Au(I) centre, [55][56][57][58][59][60][61][62][63][64] its extension to far less reactive CÀ H bonds is yet to be realized. As far as σ-bond metathesis is concerned, the viability of such processes in gold catalysis has been shown by Nolan and co-workers for the activation of acidic CÀ H bonds of alkynes, fluorobenzenes, and heteroarenes in the presence of NHC-ligated gold(I) hydroxide complexes.…”

Section: Introduction 1gold-catalyzed Cà H Functionalization Reactionsmentioning

confidence: 99%

Enantioselective C−H Functionalization Reactions under Gold Catalysis

Patil

Das

2022

Chemistry A European J

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Transition metal-catalyzed enantioselective functionalization of ubiquitous CÀ H bonds has proven to be promising field as it offers the construction of chiral molecular complexity in a step-and atom-economical manner. In recent years, gold has emerged as an attractive contender for catalyzing such reactions. The unique reactivities and selectivities offered by gold catalysts have been exploited to access numerous asymmetric transformations based on gold-catalyzed CÀ H functionalization processes. Herein, this review critically highlights the major advances and discoveries made in the enantioselective CÀ H functionalization under gold catalysis which is accompanied by mechanistic insights at appropriate places.

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“…The ligand-enabled oxidative addition of aryl iodides has been used as entry point to achieve catalytic C–C and C–N cross-couplings such as the arylation of indoles, of anilines and (sulfon)amides. 5 a – c It has also been successfully merged with π activation, enabling the difunctionalization of alkenes (heteroarylation, diarylation). 5 d – g ,6 In addition, the (P,N) aryl Au( iii ) proved very powerful and chemoselective to arylate cysteine residues of peptides and proteins, as well as to derivatize B-cages and access well-defined hybrid nanoclusters.…”

Section: Introductionmentioning

confidence: 99%