Cobalt-catalyzed arylation of aldimines via directed C–H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines

Gao, Ke; Yoshikai, Naohiko

doi:10.1039/c2cc31114c

Cited by 118 publications

(64 citation statements)

References 54 publications

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“…Proto-demetallation with a molecule of 2-phenylpyridine furnishes the desired product and regenerates intermediate 1. This mechanism is distinct from the analogous low-valent cobalt catalyzed addition to imines in that it does not require an organometallic base to facilitate C-H activation [44].…”

Section: Cobalt Catalysismentioning

confidence: 99%

High-Valent Co(III)- and Ni(II)-Catalyzed C–H Activation

Hyster

2014

Catal Lett

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The past two decades have witnessed explosive growth in the field of catalytic C-H activation. While this reactivity is typically associated with second-and thirdrow transition metals, first-row transition metals are also capable of catalyzing these reactions. C-H activation reactions can be further divided into ones where the C-H activation occurs with a low-valent metal and those where the activation occurs with a high-valent metal. This review will summarize advances in the area of high-valent Co(III)-and Ni(II)-catalyzed C-H activation with particular emphasis paid to how these catalysts compare their secondand third-row congeners.

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Section: Cobalt Catalysismentioning

confidence: 99%

High-Valent Co(III)- and Ni(II)-Catalyzed C–H Activation

Hyster

2014

Catal Lett

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“…Yoshikai et al developed an addition reaction of arylpyridines 3 to imines using low-valent cobalt catalyst generated from CoCl 2 , IPr · HCl, and t- BuMgBr (Scheme 35) [95]. The reaction tolerated a wide range of arylpyridines and aldimines, giving diarylmethylamines 57 in good yields.…”

Section: Reviewmentioning

confidence: 99%

Hydroarylations by cobalt-catalyzed C–H activation

Santhoshkumar¹,

Cheng²

2018

Beilstein J. Org. Chem.

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As an earth-abundant first-row transition metal, cobalt catalysts offer a broad range of economical methods for organic transformations via C–H activation. One of the transformations is the addition of C–H to C–X multiple bonds to afford alkylation, alkenation, amidation, and cyclization products using low- or high-valent cobalt catalysts. This hydroarylation is an efficient approach to build new C–C bonds in a 100% atom-economical manner. In this review, the recent developments of Co-catalyzed hydroarylation reactions and their mechanistic studies are summarized.

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“…Low-valent cobalt catalysts are known to be efficient in C-H functionalization, such as hydroarylation of olefins [7,8], C-H/electrophiles coupling [9,10], addition of arylzinc reagents to alkynes [11,12]. For these reactions, it is speculated that the mechanism proceeds through a Co 1? intermediate and an oxidative addition/reductive elimination pathway.…”

Section: Introductionmentioning

confidence: 99%

Studies on the Nature of Active Cobalt Species for the Production of Methane and Propylene in Catalytic Dehydrogenation of Propane

Sun

Shan

et al. 2015

Catal Lett

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Co/Al 2 O 3 catalysts with different Co 3 O 4 loadings were studied in catalytic dehydrogenation of propane. The optimal results of 21.5 wt% propylene yield and 83.6 % selectivity were obtained at 5 wt% loading. XRD, DRS and XPS results showed that at loadings below 10 wt%, the ''surface Co spinel'' formed from tetrahedral Co 2? ions during the course of reaction constituted the active site for dehydrogenation reaction. Whereas at high loadings (above 10 wt%), only Co 3 O 4 crystallites presented, which were easily reduced to metallic Co species, resulting in dramatically enhanced cracking reaction and the formation of abundant methane. Graphical AbstractElectronic supplementary material The online version of this article (

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Cobalt-catalyzed arylation of aldimines via directed C–H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines

Abstract: A cobalt-N-heterocyclic carbene catalyst, in combination with an appropriate Grignard reagent, promotes a chelation-assisted aromatic C-H functionalization reaction via addition to an aromatic aldimine.

Cited by 118 publications

References 54 publications

High-Valent Co(III)- and Ni(II)-Catalyzed C–H Activation

High-Valent Co(III)- and Ni(II)-Catalyzed C–H Activation

Hydroarylations by cobalt-catalyzed C–H activation

Studies on the Nature of Active Cobalt Species for the Production of Methane and Propylene in Catalytic Dehydrogenation of Propane

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