Enantioselective catalysis of Suzuki reaction with planar-chiral CN-palladacycles: competition of two catalytic cycles

Gorunova, O. N.; Grishin, Yuri K.; Ilyin, M. M.; Кочетков, К. А.; Churakov, Andrei V.; ́mina, L. G. Kuz; Dunina, V. V.

doi:10.1007/s11172-017-1729-4

Cited by 12 publications

(2 citation statements)

References 145 publications

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“…Asymmetric palladium catalysed cross‐coupling reactions have been developed extensively in recent years [7] . Although chiral non‐racemic palladacycles and related pincer complexes have been applied widely for the catalytic synthesis of chiral non‐racemic compounds, [8] there are seemingly no examples of the successful use of these in enantioselective cross‐coupling reactions proceeding via a Pd(0)/Pd(II) catalytic cycle [9] …”

Section: Introductionmentioning

confidence: 99%

Application of a Ferrocene‐Based Palladacycle Precatalyst to Enantioselective Aryl‐Aryl Kumada Coupling

2022

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The palladium catalysed reaction of 1‐iodo‐2‐methylnaphthalene and 2‐methyl‐1‐naphthylmagnesium bromide gave quantitatively an (Sa)‐configured cross‐coupled product in 80 % e.e. using (R,Sp)‐PPFA as a ligand. N,N‐Dimethylaminomethylferrocene was cyclopalladated (Na2PdCl4, (S)−Ac−Phe−OH, 93 % e.e., as determined by 1H NMR as a result of self‐induced non‐equivalence), and the resulting (Sp)‐configured dimeric palladacycle was employed as a precatalyst for this cross‐coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base‐promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an (Sp)‐configured product in up to 71 % e.e.

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Section: Introductionmentioning

confidence: 99%

Application of a Ferrocene‐Based Palladacycle Precatalyst to Enantioselective Aryl‐Aryl Kumada Coupling

2022

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“…[7][8][9][10] A recent report on palladacycle catalysed asymmetric Suzuki cross-coupling was explained by the operation of a Pd(II)/Pd(IV) catalytic cycle. 12 In contrast, the use of chiral non-racemic palladacycles as precatalysts for asymmetric reactions proceeding via a Pd(0)/Pd(II) catalytic cycle does not appear to have been demonstrated. 13 In this paper we describe the use of chiral non-racemic palladacycles as precatalysts for the formation of Pd(0)/chiral ligand coordinated complexes, followed by the application of these as catalysts in asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

Planar chiral palladacycle precatalysts for asymmetric synthesis

2020

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Efficient Synthesis of Malonate Functionalized Chiral Phosphapalladacycles and their Catalytic Evaluation in Asymmetric Hydrophosphination of Chalcone

Chen

Pang

et al. 2018

Eur J Inorg Chem

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Four chiral phosphapalladacycle complexes functionalized with the malonate moiety at the chiral carbon have been synthesized via a consecutive asymmetric hydrophosphination and cyclometallation protocol. High conversions were achieved in the P-H addition reaction, which was itself catalyzed by a phosphapalladacycle. Moderate to good enantioselectivities, were obtained for this step depending on the nature of the [a] 4386 Scheme 2. Synthesis of (S [P] )-8 from racemic phosphine ligands.

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Enantioselective catalysis of Suzuki reaction with planar-chiral CN-palladacycles: competition of two catalytic cycles

Cited by 12 publications

References 145 publications

Application of a Ferrocene‐Based Palladacycle Precatalyst to Enantioselective Aryl‐Aryl Kumada Coupling

Application of a Ferrocene‐Based Palladacycle Precatalyst to Enantioselective Aryl‐Aryl Kumada Coupling

Planar chiral palladacycle precatalysts for asymmetric synthesis

Efficient Synthesis of Malonate Functionalized Chiral Phosphapalladacycles and their Catalytic Evaluation in Asymmetric Hydrophosphination of Chalcone

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