Cobalt-catalyzed C–H activation: recent progress in heterocyclic chemistry

Ujwaldev, Sankuviruthiyil M.; Harry, Nissy Ann; Divakar, Mathiyazhagan Arun; Anilkumar, Gopinathan

doi:10.1039/c8cy01418c

Cited by 94 publications

(24 citation statements)

References 114 publications

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“…Indeed, Co exhibits a comparable coordination sphere to Zn, is a cheap metal that have found ongoing developments in catalysis for example. [48][49][50][51][52] In this context, gaining a first set of structural information is undoubtedly of broad interest. The geometry of Co complexes is analyzed from solid-state data and finally compared to their Zn analogues.…”

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confidence: 99%

Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray

Large

Meddeb

Pucheta

et al. 2019

Inorganica Chimica Acta

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The preparation of pyridylmethylamines (pma)-ZnBr2 and -CoBr2 complexes is described. Accurate structural informations in both solution and solid state have been obtained using an approach combining advanced NMR such as pure shift gradient-encoded selective refocusing (PS-GSERF) and conventional NOESY experiments, DFT calculations and X-ray analysis. The methodology developed has allowed a clear identification and characterization of preferred conformations and configurations at an atomic resolution. Our study has evidenced some key features of the overall 3D structure of pma-Zn and pma-Co complexes which shapes are set by the geometry of the metallacycle, the configuration of the sp 3 nitrogen atom, the equatorial position of the benzyl side arm as well as the preferred spatial arrangement of the chiral side arm with respect to the metallacycle.

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mentioning

confidence: 99%

Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray

Large

Meddeb

Pucheta

et al. 2019

Inorganica Chimica Acta

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“…Under the optimized conditions (Scheme 4), authors investigated the substrate scope, firstly, in regard of alkynes and found that aryl substituted terminal alkynes bearing either electron-withdrawing or -donating groups on various positions of the aromatic ring afforded products in high yields (38)(39)(40)(41)(42). Moreover, terminal alkynes with aromatic substituents like naphthyl, pyrene, and heterocycles led to high yields (43)(44)(45)(46), while terminal aliphatic substituted alkynes resulted in low to high yields (47)(48)(49)(50)(51). There were only a few examples for internal alkynes with yields being low to moderate (52,53).…”

Section: Annulations Via C(sp 2 )-H Bond Activationmentioning

confidence: 99%

“…Motivated by the above-mentioned needs, researchers have employed the use of functional groups that significantly affect C-H activation reactions. Directing groups (DG) represent an ingenious way to orchestrate and manipulate atoms towards the synthesis of important classes of organic compounds, such as pyrroles, indoles, quinolines, indolinones, and related heterocycles [44][45][46][47][48]. Transition metals can temporarily coordinate to these specific sites on the starting materials, thus leading to the formation of key intermediates that would not form otherwise.…”

Section: Introductionmentioning

confidence: 99%

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

et al. 2021

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Sustainable transformations towards the production of valuable chemicals constantly attract interest, both in terms of academic and applied research. C–H activation has long been scrutinized in this regard, given that it offers a straightforward pathway to prepare compounds of great significance. In this context, directing groups (DG) have paved the way for chemical transformations that had not been achievable using traditional reactions. Few steps, high yields, selectivity and activation of inert substrates are some of the invaluable assets of directed catalysis. Additionally, the employment of traceless directing groups (TDG) greatly improves and simplifies this strategy, enabling the realization of multi-step reactions in one-pot, cascade procedures. Cheap, abundant, readily available transition metal salts and complexes can catalyze a plethora of reactions employing TDGs, usually under low catalyst loadings—rarely under stoichiometric amounts, leading in greater atom economy and milder conditions with increased yields and step-economy. This review article summarizes all the work done on TDG-assisted catalysis with manganese, iron, cobalt, nickel, or copper catalysts, and discusses the structure-activity relationships observed, by presenting the catalytic pathways and range of transformations reported thus far.

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“…The capability of manganese as a promising catalyst is evident from the reports in oxidation [15], reduction [16], C‐H activation [17], coupling reactions [18], etc. In continuation of our constant interest in green reactions and earth abundant transition metal catalyzed processes, we focused on microwave (MW) reactions [19] and transition metal catalysis involving Fe [20], Co [21], Ni [22], Mn [23], and Cu [24], respectively. As an extension, we herein report the first manganese‐catalyzed strategy for N ‐aryl pyrrole synthesis using a green Clauson‐Kaas protocol under microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

A solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas protocol for the synthesis of N‐aryl pyrroles under microwave irradiation

Rohit

Meera

Anilkumar

2021

Journal of Heterocyclic Chem

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The first manganese‐catalyzed modified Clauson‐Kaas reaction for N‐substituted pyrrole synthesis using 2,5‐dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co‐catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20 min). The above qualities attest to the green nature of this reaction.

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Cobalt-catalyzed C–H activation: recent progress in heterocyclic chemistry

Abstract: Cobalt-catalyzed C–H activation has gone through some major advancements in the past couple of decades.

Cited by 94 publications

References 114 publications

Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray

Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

A solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas protocol for the synthesis of N‐aryl pyrroles under microwave irradiation

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