Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions

Banerjee, Somsuvra; Patil, Nitin T.

doi:10.1039/c7cc04283c

Cited by 49 publications

(27 citation statements)

References 49 publications

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“…[204] The methodology may be seen as the Au-catalyzed version of the well-known Cadiot-Chodkiewicz reaction. [206] They used Au(PPh 3 )Cl and phen as the cooperative catalytic systemsf or performing the reactions. It is expected that the Au catalyst, Ag additives, and phenel igands( 1,10-phenanthroline) cooperatively activate the reaction.T wo possible mechanisms for the heterocoupling are shown in Scheme 28.…”

Section: Hypervalent Iodine As the Oxidant For Mediating Au I / Au Iimentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

142

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Transition-metal-catalyzed cross-couplingr eactions are central to many organic synthesis methodologies. Traditionally,P d, Ni, Cu, and Fe catalysts are used to promote these reactions. Recently,m any studies have showedt hat both homogeneous and heterogeneous Au catalysts can be used for activating selective cross-coupling reactions.H ere, an overview of the past studies, current trends, andf uture directions in the field of gold-catalyzed coupling reactions is presented.D esign strategiest oa ccomplish selective homocoupling and cross-coupling reactions under both homogeneous and heterogeneous conditions, computational and ex-perimental mechanistic studies, and their applicationsi nd iverse fields are critically reviewed. Specific topics covered are:o xidant-assisted and oxidant-free reactions;s train-assisted reactions;d ual Au and photoredoxc atalysis;b imetallic synergistic reactions;m echanismso fr eductivee limination processes;e nzyme-mimicking Au chemistry;c lustera nd surface reactions;a nd plasmonic catalysis. In the relevant sections, theoretical and computational studies of Au I /Au III chemistry are discussed and the predictionsf rom the calculationsa re compared with the experimental observations to derive useful design strategies.A. Nijamudheen earnedh is PhD from IACS, Kolkata,i n2 015. Currently,h ei sapostdoctoral researcher atF loridaS tate University.H is researchi nterests are in computational catalysis, solar energym aterials, and beyond Li-ion battery technologies.Ayan Dattai sc urrently aP rofessor at IACS, Kolkata.H is research interests include theoretical and computational studieso ft ransitionmetal-catalyzed reactions,o pto-electronic properties of organic and solid-statem aterials, and the design of renewableenergymaterials. He has won several awards including the DST-SERB Distinguished Investigator Award (DIA) in 2019.

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Section: Hypervalent Iodine As the Oxidant For Mediating Au I / Au Iimentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

142

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“…As an alkynylated reagent, EBXs have been widely used in an intermolecular alkynylation reaction [3, 9, 10] . For example, EBXs reacted with terminal alkynes to provide 1,3‐diynes under gold‐catalyzed or n BuLi‐promoted condition, which were reported by the groups of Liu, [10a] Patil [3a] and Waser, [10b] respectively (Scheme 1 B). The major drawback of these methods is the formation of one equivalent of “waste” 2‐iodobenzoic acid or (2‐iodophenyl)methanol (Scheme 1 A and B).…”

Section: Figurementioning

confidence: 84%

Synthesis, Characterization of Spirocyclic λ³‐Iodanes and Their Application to Prepare 4,1‐Benzoxazepine‐2,5‐diones and 1,3‐Diynes

Sun

Guo

Chen

et al. 2021

Chemistry A European J

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Herein, a [3+2] cycloaddition of aza‐oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3‐iodanes containing spirocyclic 4‐oxazolidinone has been developed. This cyclic λ3‐iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1‐benzoxazepine‐2,5‐diones and symmetrical 1,3‐diynes derivatives were afforded in high yield under copper(I)‐catalyzed conditions.

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“…[89] In 2017, Patil and coworkers reported the gold-catalyzed C(sp)À C(sp) alkynylation of terminal alkynes with EBXs to access unsymmetric 1,3-diynes (Figure 15b). [90] They used Ph 3 PAuCl as catalyst and catalytic amount of 1,10phenanthroline as auxiliary ligand. Likewise, the group of Liu also used alkynyl hypervalent iodine reagents in the coupling with terminal alkynes for the synthesis of unsymmetrical 1,3diynes.…”

Section: Coupling Partners With Dual Rolementioning

confidence: 99%

“…Computational studies on the mechanism of this domino reaction revealed that the Au(III) catalyst was the precursor of the active Au(I) catalyst that initiates the Au(I)/Au(III) catalytic cycle [89] . In 2017, Patil and coworkers reported the gold‐catalyzed C(sp)−C(sp) alkynylation of terminal alkynes with EBXs to access unsymmetric 1,3‐diynes (Figure 15b) [90] . They used Ph 3 PAuCl as catalyst and catalytic amount of 1,10‐phenanthroline as auxiliary ligand.…”

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

confidence: 99%

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

Font

Ribas

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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Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions

Cited by 49 publications

References 49 publications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Synthesis, Characterization of Spirocyclic λ³‐Iodanes and Their Application to Prepare 4,1‐Benzoxazepine‐2,5‐diones and 1,3‐Diynes

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

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Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions

Cited by 49 publications

References 49 publications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Synthesis, Characterization of Spirocyclic λ3‐Iodanes and Their Application to Prepare 4,1‐Benzoxazepine‐2,5‐diones and 1,3‐Diynes

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

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Synthesis, Characterization of Spirocyclic λ³‐Iodanes and Their Application to Prepare 4,1‐Benzoxazepine‐2,5‐diones and 1,3‐Diynes