Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling

Wu, Linglin; Salvador, Alvaro; Ou, Arnold; Shi, M.; Skelton, Brian W.; Dorta, Reto

doi:10.1055/s-0033-1338864

Cited by 28 publications

(2 citation statements)

References 3 publications

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“…Chiral NHC complexes with naphthyl side chains were synthesized by Dorta et al Complex C60 revealed high yield (up to 94%) and moderate enantioselectivities (up to 60% ee). 91 PEPSI complex C61 showed good catalytic activity and moderate to good enantioselectivities in asymmetric Suzuki coupling (80% ee). 92 Enantiomeric excesses, up to 46%, have been obtained in the palladium-catalyzed asymmetric Suzuki-Miyaura reaction using very bulky (benz)imidazole-2-ylidene ligands (C62 and C63).…”

Section: Figurementioning

confidence: 99%

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Gürbüz¹,

Karaca²,

Özdemır³

et al. 2015

Turk J Chem

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This review is focused on new developments reported during the last 3 years concerning the catalytic performances of in situ formed or preformed NHC-Pd(II) complexes (NHC: N -heterocyclic carbene) for cross-coupling reactions such as Heck-Mizoraki (often shortened to the Heck reaction), Kumada, Negishi, Suzuki-Miyaura (often shortened to the Suzuki reaction), Sonogashira and Hiyama couplings, and the Buchwald-Hartwig aminations, which are extremely powerful in the formation of C-C and C-heteroatom bonds. Due to the great number of publications and limited space here, we made a special attempt to compile the relevant data in tables, which we hope will serve as a guide for chemists interested in these reactions. The syntheses of the precatalysts and the generally accepted reaction mechanisms are also briefly described.

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Section: Figurementioning

confidence: 99%

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Gürbüz¹,

Karaca²,

Özdemır³

et al. 2015

Turk J Chem

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“…In 2000, the pioneering reports of the groups Cammidge 3 and Buckwald 4 on Pd-catalyzed asymmetric SMC reactions demonstrated the possibility of utilizing substrates and/or chiral ligands enabled enantio-convergent transformation to gain access to biaryl atropisomers from commercially available and bench-stable substrates. Since then, tremendous progress has been made in this field and a series of phosphine, bis-Hydrazone, N-heterocyclic carbene (NHC) and diene based chiral ligands were developed by groups of Qiu 5 , Wu and Zhang 6 , Tang 7 , Byrne and Smith 8 , Fernández and Lassaletta 9 , Lin 10 , Dorta 11 and Shi 12 to improve enantioselectivity as well as expand the substrate scope of asymmetric Pd-SMC. In addition, various novel approaches introducing bio 13 or heterogeneous 14 catalysis have been proved to achieve moderate to excellent enantiocontrol.…”

Section: Introductionmentioning

confidence: 99%

Data-Driven Phosphine Ligand Design of Ni-Catalyzed Enantioselective Suzuki–Miyaura Cross-Coupling Reaction for the Synthesis of Biaryl Atropisomers: standing on the shoulder of Pd catalysis giants

Xu,

Liu

et al. 2024

Preprint

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The Suzuki-Miyaura cross-coupling reaction is a cornerstone in organic synthesis, enabling the formation of carbon–carbon bonds with high efficiency and selectivity. This study represents a groundbreaking advancement in the field by pioneering the first enantioselective Ni-catalyzed Suzuki–Miyaura cross-coupling reactions for the synthesis of biaryl atropisomers. Employing a data-driven approach, we have crafted a novel N-protected Xiao-Phos ligand, which, in conjunction with commercially available Ni(COD)2, delivered unparalleled enantioselectivity and reactivity under mild conditions. The ligand design was meticulously guided by an extensive examination of the existing literature on Pd-catalyzed asymmetric Suzuki–Miyaura cross-coupling reactions, directing the virtual screening and subsequent experimental verification of the synthesized ligands in a single iteration. The innovative ligand N-Bn-Xiao-Phos exhibited impressive enantioselectivities coupled with exceptional yields, showcasing versatility with a diverse array of functional groups and aryl boronic acids, and accomplishing successful gram-scale synthesis. DFT computational studies provided profound insights into the reaction mechanism and the roots of enantioselectivity, elucidating the dynamic coordination modes of the chiral ligand and the steric induction. This breakthrough not only broadens the horizons of Ni-catalyzed cross-coupling reactions but also highlights the immense potential of machine learning in the judicious design of chiral ligands for asymmetric synthesis.

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Metal‐Catalyzed Asymmetric Synthesis of Biaryl Atropisomers

Zhou

Shi

2021

Axially Chiral Compounds

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Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling

Cited by 28 publications

References 3 publications

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Data-Driven Phosphine Ligand Design of Ni-Catalyzed Enantioselective Suzuki–Miyaura Cross-Coupling Reaction for the Synthesis of Biaryl Atropisomers: standing on the shoulder of Pd catalysis giants

Metal‐Catalyzed Asymmetric Synthesis of Biaryl Atropisomers

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