Nickel-catalyzed C–H/N–H annulation of aromatic amides with alkynes in the absence of a specific chelation system

Obata, Atsushi; Ano, Yusuke; Chatani, Naoto

doi:10.1039/c7sc01750b

Cited by 68 publications

(43 citation statements)

References 65 publications

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“…Ni-catalyzed methylation of C(sp 2 )-H bond with dicumyl peroxide (Chatani et al, 2016) [38e] Scheme 29 Ni-catalyzed benzylation of C(sp 2 )-H bond with benzyltrimethylammonium bromide (Chatani et al, 2017) [39a] Despite the undisputed advances made in the Ni(II)-catalyzed C-H alkylation, earlier reports were largely limited to carboxylic acid derivatives assisted by N,N-bidentate directing groups (e.g., AQ and PIP).…”

Section: Scheme 28mentioning

confidence: 99%

Ni‐Catalyzed Chelation‐AssistedDirect Functionalization of Inert C—H Bonds

2020

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During the last two decades, impressive advancements have been achieved in transition metal-catalyzed chelation-assisted C-H functionalization reaction. While reactions in this field are still dominated by precious 4d or 5d metals (e.g., Pd, Rh, Ir), the 3d base metals (e.g., Ni, Co, Cu, Fe) have made significant headway partially due to their relatively large abundance, low cost, low toxicity as well as their occasionally occurred novel reactivity when compared to their noble cousins. This review will give a comprehensive summary on Ni-catalyzed functionalization of inert C-H bonds assisted by chelation groups. For clarity, the content is classified by the newly formed chemical bonds, namely C-C, C-N, C-chalcogen and C-halogen bond formation.Yan-Hua Liu (left) received his B.S. degree in 2013 from North University of China. Then he pursued his Ph.D. degree under the supervision of Prof. Bing-Feng Shi in organic chemistry at Zhejiang University. His current research is focused on transition-metal-catalyzed enantioselective C-H bond activation.

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Section: Scheme 28mentioning

confidence: 99%

Ni‐Catalyzed Chelation‐AssistedDirect Functionalization of Inert C—H Bonds

2020

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“…Diferentes alcinos também foram utilizados, e rendimentos entre <5% e 77% foram obtidos através de uma mistura de regioisômeros que variou entre 3:1 até a obtenção de apenas um isômero. 28 Com intuito de determinar o mecanismo, experimentos controle foram executados, como a reação com marcação isotópica de deutério, que não foi possível observar troca de H/D no produto e na amida recuperada. Assim, conclui-se que a clivagem da ligação C-H é irreversível.…”

Section: Esquema 21 Ciclo Catalítico Proposto Para Reação De Alquilaunclassified

“…Pode-se observar também que a função do alcino não é de apenas componente de acoplamento, ele também é um aceptor de hidrogênio. 28 De 28 Wei e colaboradores desenvolveram um método para a clivagem de ligações sp 2 C-H e C-N, catalisadas por níquel, na reação entre amidas aromáticas contendo 8-aminoquinolinas com sais de amônio benzílico. Após otimizar as condições reacionais, uma varredura do contra ânion foi investigada.…”

Section: Esquema 21 Ciclo Catalítico Proposto Para Reação De Alquilaunclassified

Recentes Avanços Em Reações Orgânicas Catalisadas Por Níquel

Pinheiro¹,

Amarante²

2018

Quim. Nova

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publicado na web em 31/07/2018 RECENT ADVANCES IN ORGANIC REACTIONS CATALYZED BY NICKEL. Nickel complexes have been widely used as catalysts in organic reactions. Their low price compared to Pd and Pt complexes, in addition to their high reactivity and affinity to π systems; the possibility to access different oxidation states and the difficulty to undergo beta-hydride elimination are important features that have attracted the attention of chemists in recent decades. Furthermore, some drawbacks observed with Pd catalysis have been solved by Ni catalysis. These Ni based-catalysts have been used in different reaction manifolds to promote challenging transformations. Herein, recent work using nickel catalysts in different types of reactions, such as carbonylations, carboxylations, C-H activations and dual catalytic systems are described. Critical mechanistic investigations, as well as synthetic applications are also covered.

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“…Despite great achievements in the realm of C-H annulation, the challenge of realizing the direct C-H annulation of arenes and alkenes by using inexpensive metal catalyst still remains. 4 Cobalt has been widely used as a catalyst in various C-H bond functionalization reactions due to its unique catalytic reactivity and being inexpensive with low toxicity. 5 Signicant efforts have been made to achieve Co-catalyzed C-H activation to construct C-C and C-X bonds, as pioneered by Yoshikai, 6 Matsunaga/Kanai, 7 Daugulis, 8 Ackermann 9 and others, 10 further proving the excellent catalytic properties of cobalt catalysts.…”

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confidence: 99%