Palladium‐Catalyzed Dearomative Cyclocarbonylation by CN Bond Activation

Yu, Hui; Zhang, Guoying; Huang, Hanmin

doi:10.1002/ange.201504805

Cited by 19 publications

(2 citation statements)

References 64 publications

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“…The wide bite angle and flexible coordination environment of Xantphos 24 are factors responsible for making it highly efficient ligand among other large bite angle diphosphines such as DPEphos (bis(2-diphenylphosphinophenyl)ether), dppf (1,1′bis(diphenylphosphino)ferrocene), or Binap (2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl) in catalysis reactions. 25,26 We have investigated the reactions of [M′(Xantphos)-(OTf) 2 ] and arylenedithiols of varying position of thiol groups as bridging ligands (Scheme 1). Interestingly, the 31 P NMR spectrum of the resulted Pd and Pt complexes showed two distinct signals indicating the presence of two species in solution.…”

Section: ■ Introductionmentioning

confidence: 99%

Xantphos-Capped Pd(II) and Pt(II) Macrocycles of Aryldithiolates: Structural Variation and Catalysis in C–C Coupling Reaction

et al. 2019

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The self-assembly of Xantphos-capped M(OTf)2 (M = cis-[M′(Xantphos)]2+; M′ = Pd, Pt) with bridging ligands 1,4-benezenedithiol or 4,4′-biphenyldithiol has been investigated. The reactions have yielded complexes [M{S(C6H4) n SH}]2(OTf)2 (I) and [M 2{S(C6H4) n S}]2(OTf)4 (II) (n = 1 or 2). The equilibrium between I and II has been established in platinum complexes for n = 2, whereas the analogous Pd complex exclusively exist as II. These results are different from our previously reported dppe or triethyl phosphine-capped complexes which showed only type II. The same reaction with 1,3-benezenedithiol lead to the complex [M 2(SC6H4SSC6H4S)](OTf)2 (III), containing a S–S bond between two thiolate ligands, formed via a complex of type I in solution. Characterization of the complexes was accomplished by NMR spectroscopy, UV–vis spectroscopy and mass spectrometry, and X-ray crystallography. Density functional calculations were performed to estimate the relative stability of three types of complexes. The palladium complexes are excellent catalysts in Suzuki C–C cross coupling reactions under mild conditions, and can be reused eight times without losing significant yield. The activity of the Pd catalysts derived from three dithiol ligand follows opposite trend of the stability as III > II > I. The comparative catalytic activity of the tetranuclear Pd complexes (II) of bis-phosphines of varied bite angles, including the structurally characterized [Pd2(dppf)2(SC12H8S)]2(OTf)4 has also been demonstrated.

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Section: ■ Introductionmentioning

confidence: 99%

Xantphos-Capped Pd(II) and Pt(II) Macrocycles of Aryldithiolates: Structural Variation and Catalysis in C–C Coupling Reaction

et al. 2019

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“…Allylamines, especially those with easy-to-transform functional groups, are an indispensable class of building blocks in the field of organic synthesis and the pharmaceutical industry (1). Typically, they are also the versatile synthetic intermediates in the atomic economical construction of alkaloids, amino acids, and complex natural products (2)(3)(4). A wide range of drug molecules (5-7) could be obtained by the derivatization of allylamines (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of medicinally relevant oxalylamines via copper/Lewis acid synergistic catalysis

Jin

et al. 2021

Sci. Adv.

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Allylamines have long been recognized as valuable synthons because of their excellent reactivity in organic synthesis. Here, an efficient amination reaction of allenyl ethers via copper/Lewis acid synergistic catalysis has been established, providing straightforward access to diverse functionalized Z-oxalylamines and E-halogenated oxalylamines in good to excellent yields with high regio- and stereoselectivities. The developed method tolerates more than 100 examples that include late-stage functionalization of bioactive molecules, and features gram-scale synthesis of oxalylamines with high turnover number (TON > 1000) under mild and simple conditions. The applicability of the protocol is further demonstrated with the construction of drug molecules.

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Palladium‐Catalyzed Stereospecific Allylation of Nitroacetates with Enantioenriched Primary Allylic Amines

Wang

et al. 2016

Adv Synth Catal

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An unprecedented stereospecific allylation reactiono fn itroacetates with enantioenriched primary allylica mines has been developed. Ar ange of nitroacetates smoothly underwent allylation with enantioenriched primary allylic aminesi nt he presence of ap alladium catalyst and boric acid followed by one-pot decarboxylation to afford structurallydiverse homoallylic nitro compounds in good to excellent yields with excellent retention of configuration. On the other hand, the allylation followed by denitronation provided af acile synthetic route to optically active b-chiral g,d-unsaturated esters.

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Palladium‐Catalyzed Dearomative Cyclocarbonylation by CN Bond Activation

Cited by 19 publications

References 64 publications

Xantphos-Capped Pd(II) and Pt(II) Macrocycles of Aryldithiolates: Structural Variation and Catalysis in C–C Coupling Reaction

Xantphos-Capped Pd(II) and Pt(II) Macrocycles of Aryldithiolates: Structural Variation and Catalysis in C–C Coupling Reaction

Synthesis of medicinally relevant oxalylamines via copper/Lewis acid synergistic catalysis

Palladium‐Catalyzed Stereospecific Allylation of Nitroacetates with Enantioenriched Primary Allylic Amines

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