Ru-catalysed C–H functionalisations as a tool for selective organic synthesis

Ruiz, Sara; Villuendas, Pedro; Urriolabeitia, Esteban P.

doi:10.1016/j.tetlet.2016.06.117

Cited by 66 publications

(12 citation statements)

References 174 publications

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“…The development of economical C–H functionalization methods has always been the aim of researchers’ efforts, and ruthenium catalysts are highly valued by researchers due to their versatility and relatively low price . Moreover, the ruthenium‐catalyzed C–H functionalization with amides as the directing group has been widely used.…”

Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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Since the beginning of the 21st century, significant progress has been made in transition metal‐catalyzed C–H functionalization of aromatic amides. The achievements in this field have mainly focused on ortho (proximal) functionalization, there have been far fewer reports on remote C–H functionalization, and para‐ and meta‐selective functionalizations remain a major challenge. Interestingly, there are few related comments in this field. In a few published cases, the scope of the report is relatively narrow, either to comment on the functionalization of a specific directing group or to summarize the functionalization of a specific reaction site. Herein, for the first time, we have comprehensively summarized the C–H functionalization of aromatic amides. This review is divided into three parts: ortho‐, para‐ and meta‐C–H functionalization of aromatic amides, and is subdivided according to the type of catalyst. The directing groups, reaction types, conditions, mechanism and applications of the corresponding reactions are discussed in detail.

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Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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“…The versatility of Ru, as well as its considerably lower price compared to other 2nd and 3rd-row transition metals, make it an appealing candidate around which to develop economical C-H functionalization methodology [ 34 , 35 ]. Moreover, considerable advances have been made in Ru-catalyzed C-H functionalization directed by weakly coordinating groups, including amides [ 33 ].…”

Section: Ru-catalyzed Reactionsmentioning

confidence: 99%

Weinreb Amides as Directing Groups for Transition Metal-Catalyzed C-H Functionalizations

Kalepu

Pilarski

2019

Molecules

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Weinreb amides are a privileged, multi-functional group with well-established utility in classical synthesis. Recently, several studies have demonstrated the use of Weinreb amides as interesting substrates in transition metal-catalyzed C-H functionalization reactions. Herein, we review this part of the literature, including the metal catalysts, transformations explored so far and specific insights from mechanistic studies.

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“…Heteroarylation via C-H bond activation has been largely applied to material science, for example, the synthesis of conjugated dyes [8] and polymers [9]. Although Pd [10][11][12][13][14] and Rh [15][16][17][18] catalysts are very efficient in enabling the selective functionalization of C-H bonds, the use of easy-to-prepare, air-stable, often stable in water and functional groups tolerant Ru(II) complexes have attracted much interest in the development of efficient catalytic systems for these processes [19][20][21][22][23][24][25][26]. Despite the ubiquity of C-H bonds in organic molecules, the regioselectivity of C-H bond functionalization can elegantly be controlled by chelation assistance of directing groups [27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?

et al. 2020

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Ru(II)/carboxylate/PPh3 catalyst system enabled the preparation of highly conjugated pyrazine derivatives in water under microwave irradiation. Both nitrogen atoms efficiently dictated cleavage of the ortho-C–H bonds in both benzene rings of 2,3-diphenylpyrazine substrates through chelation assistance. In conformationally more flexible diphenyldihydropyrazine 1, the arylation of four ortho-C–H bonds was possible, while in the aromatic analog 2, the triarylation was the limit.

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Ru-catalysed C–H functionalisations as a tool for selective organic synthesis

Cited by 66 publications

References 174 publications

C–H Functionalization of Aromatic Amides

C–H Functionalization of Aromatic Amides

Weinreb Amides as Directing Groups for Transition Metal-Catalyzed C-H Functionalizations

Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?

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