Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR3)2Pd(II)X2] Precatalysts

Ma, Siyue; Zhou, Tongliang; Li, Guangchen; Szostak, Michal

doi:10.1002/adsc.202000122

Cited by 15 publications

(4 citation statements)

References 78 publications

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“…[155] The air-stable [Pd(dippf)(maleimide)] complex was used at low 0.2 mol% catalytic loadings for the selective synthesis of various di-and tertiary amines, building blocks towards highly the formation of conjugated π electron-rich structures as OLED hole transporters. [129] Scheme 38: Pd(dippf)L catalyst for sequential arylation of primary anilines.…”

Section: C-n Bond Formationmentioning

confidence: 99%

Phosphine ligands based on the ferrocenyl platform: Advances in catalytic cross-couplings

Bandaru¹,

Shah

Bhilare

et al. 2023

Coordination Chemistry Reviews

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Section: C-n Bond Formationmentioning

confidence: 99%

Phosphine ligands based on the ferrocenyl platform: Advances in catalytic cross-couplings

Bandaru¹,

Shah

Bhilare

et al. 2023

Coordination Chemistry Reviews

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“…The reaction highlights the potential of NHC ligands in the Pd‐catalyzed coupling of stable acyl electrophiles [4,14a] . For N‐benzoyl‐δ‐valerolactam, researchers selected three different systems: Pd‐NHC systems,(allyl‐based [Pd(IPr)(cin)Cl] [22] and heterocycle‐based [Pd‐PEPPSI‐IPr] [34] ), [Pd(PCy 3 ) 2 Cl 2 ] 2 [35] as a well‐defined Pd(II)‐phosphine system and in situ‐formed Pd(OAc) 2 /PCy 3 system. Finally, N‐acyl‐δ‐valerolactam showed excellent conversion under Pd‐NHC conditions (Scheme 7).…”

Section: Pd‐nhc Compounds With Symmetric Imidazolium‐base Nhc Ligandsmentioning

confidence: 99%

Recent Development in the Catalytic Applications of Pd‐NHC (NHC=N‐Heterocyclic Carbene) Compounds in Amide C−N Activation Reactions

Lin

et al. 2023

Asian J Org Chem

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Palladium‐catalyzed C−N bond activation of amide is a important but very challenging research area in organic chemistry. This reaction represents a powerful and straightforward method for the preparation of various carbonyl compounds under mild reaction conditions. One notable advancement in this area is related to the design and development of multifunctional NHC ligands and other throw‐away ligands. The reasonable design of ligands could not only improve the activity of catalyst, but also help to adjust the reaction selectivity. In this review, we summarized the structure‐activity relationship of those catalysts with different ligand skeletons and their applications in cross‐coupling reactions including Suzuki‐Miyaura coupling, Buchwald‐Hartwig amination and direct C−H acylation, via amide C−N bond activation. On this basis, we analyze the current bottlenecks encountered in Pd‐NHC‐catalyzed amide C−N activation reactions, and envisage the future development of this field.

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“…Well-defined Pd(II)–NHC catalytic systems, including different NHC ligands, have been developed for acyl C–C and C–N cross-couplings of activated amides. − …”

Section: Amide N–c Bond Activation: Abundance Of Manifolds Enabled By...mentioning

confidence: 99%

Classes of Amides that Undergo Selective N–C Amide Bond Activation: The Emergence of Ground-State Destabilization

et al. 2022

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Ground-state destabilization of the N−C(O) linkage represents a powerful tool to functionalize the historically inert amide bond. This burgeoning reaction manifold relies on the availability of amide bond precursors that participate in weakening of the n N → π* C=O conjugation through N−C twisting, N pyramidalization, and n N electronic delocalization. Since 2015, acyl N−C amide bond activation through ground-state destabilization of the amide bond has been achieved by transition-metal-catalyzed oxidative addition of the N−C(O) bond, generation of acyl radicals, and transition-metal-free acyl addition. This Perspective summarizes contributions of our laboratory in the development of new ground-state-destabilized amide precursors enabled by twist and electronic activation of the amide bond and synthetic utility of ground-state-destabilized amides in cross-coupling reactions and acyl addition reactions. The use of ground-state-destabilized amides as electrophiles enables a plethora of previously unknown transformations of the amide bond, such as acyl coupling, decarbonylative coupling, radical coupling, and transition-metal-free coupling to forge new

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Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR₃)₂Pd(II)X₂] Precatalysts

Cited by 15 publications

References 78 publications

Phosphine ligands based on the ferrocenyl platform: Advances in catalytic cross-couplings

Phosphine ligands based on the ferrocenyl platform: Advances in catalytic cross-couplings

Recent Development in the Catalytic Applications of Pd‐NHC (NHC=N‐Heterocyclic Carbene) Compounds in Amide C−N Activation Reactions

Classes of Amides that Undergo Selective N–C Amide Bond Activation: The Emergence of Ground-State Destabilization

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