Highly active homoleptic nickel(II) bis-N-heterocyclic carbene catalyst for Suzuki–Miyaura and Heck cross-coupling reactions

Nirmala, Muthukumaran; Sathyanarayana, Arruri; Vaddamanu, Moulali; Karupnaswamy, Ramesh; Mannarsamy, Maruthupandi; Adinarayana, Mannem; Prabusankar, Ganesan

doi:10.1016/j.poly.2018.10.028

Cited by 10 publications

(4 citation statements)

References 24 publications

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“…1 H NMR (500 MHz, CDCl 3 ) δ 7.53 (d, J = 8.0 Hz, 2H), 7.43 (d, J = 7.5 Hz, 1H), 7.39–7.36 (m, 2H), 7.30–7.26 (m, 1H), 7.19 (d, J = 16.5 Hz, 1H), 7.14–7.11 (m, 1H), 7.01 (d, J = 16.0 Hz, 1H), 6.86–6.83 (m, 1H), 6.75 (d, J = 8.0 Hz, 1H), 3.91 (s, 2H); 13 C{ 1 H} NMR (125 MHz, CDCl 3 ) δ 143.8, 137.6, 130.4, 128.7, 128.6, 127.5, 127.2, 126.4, 124.3, 124.0, 119.3, 116.3. Spectroscopic data for the title compound were consistent with those reported in the literature …”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

et al. 2020

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A novel metal-free one-pot protocol for the synthesis of potential biologically active molecules 3-selenylindoles via intramolecular cyclization/selenylation with simple 2-vinylaniline has been developed with moderate to good yield, thus representing it as a facile route to diverse substitution patterns around the indole core. The reaction proceeded smoothly with a broad substrate scope and excellent functional group tolerance. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Mechanistic studies have revealed that in situ formed selenium electrophile species may be the key intermediate for the selenocyclization process.

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Section: Methodsmentioning

confidence: 99%

Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

et al. 2020

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“…[9][10] In the majority of cases, the trans or E-nitrostilbene was formed as a major isomer over cis or Z-nitrostilbene from all the three positional isomers of nitrobenzaldehyde, ortho-nitrobenzalde-hyde, meta-nitrobenzaldehyde, and para-nitrobenzaldehyde (Figure 1). [1][2][3][4][5][6][7][8][9][10] Unlike meta/para-substituted-benzaldehydes, the general olefin stereoselectivity in the case of ortho-substituted benzaldehydes possessing β-hetero-atom or group usually provides cis or Z-selective stilbenes due to the ancillary phosphorus coordination with hetero-atom or group. [11][12] Rebutting the ancillary phosphorus coordination hypothesis, a qualitative analysis conducted by Marcin Stępień by utilizing density functional theory (DFT) calculations coupled with a distortion or interaction energies show that the Z-selectivity observed in Wittig olefinations of ortho-substituted benzaldehydes is mainly due to the steric reasons.…”

Section: Introductionmentioning

confidence: 99%

“…and heterocyclic compounds, nitrostilbenes have gained tremendous importance in medicinal chemistry. [ 1 , 2 ] Apart from the metal‐catalysed couplings[ 3 , 4 , 5 , 6 , 7 ] and other reactions, [8] the classical Wittig olefination method has usually been employed to synthesize these stilbenes. [ 9 , 10 ] In the majority of cases, the trans or E ‐nitrostilbene was formed as a major isomer over cis or Z ‐nitrostilbene from all the three positional isomers of nitrobenzaldehyde, ortho ‐nitrobenzaldehyde, meta ‐nitrobenzaldehyde, and para ‐nitrobenzaldehyde (Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

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Intramolecular CH‐Hydrogen Bonding During the Dissociation of the Oxaphosphetane Intermediate Facilitates Z/E‐Selectivity in Wittig Olefination

Sreenivas,

Rao,

Khan

2023

ChemistryOpen

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Herein, DFT studies corroborating experimental results revealed that the shortest intramolecular hydrogen bonding distance of cis/trans‐oxaphosphetane (OPA) oxygen with the CH‐hydrogen of a triphenylphosphine phenyl ring provides good evidence for the attained olefin Z/E‐selectivity in Wittig olefination of the studied examples. 2‐Nitrobenzaldehyde, 3‐nitrobenzaldehyde, 2‐nitro‐3‐bromobenzaldehyde, 2‐nitro‐5‐bromobenzaldehyde and 2‐nitro‐5‐arylbenzaldehydes provided Z‐nitrostilbenes with (2‐chloro‐4‐hydroxy‐3‐methoxy‐5‐(methoxycarbonyl)benzyl) triphenylphosphonium chloride as the major products. However, 4‐nitrobenzaldehyde and 2‐nitro‐6‐bromobenzaldehydes furnished E‐nitrostilbenes as the major products in high yields. Furthermore, the DFT computed intramolecular CH1/CH2‐hydrogen bond distances with Cl/NO2 of selected stilbene derivatives were in good agreement with intramolecular hydrogen bond distances measured from single‐crystal X‐ray diffraction measurements.

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Emerging Nickel Catalysis in Heck Reactions: Recent Developments

Bhakta

Ghosh

2020

Adv Synth Catal

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The synthetic application of nickel catalysts in Heck-coupling reactions is quite prominent and noticeable of late in organic synthesis. It shows great interest over the other transition metal catalysts due to its unique characteristic that prepares them more significantly applicable in different fields of synthetic application. The usefulness of nickel-catalysts relies in the fact that they are abundant in nature, relatively less precious and environment friendly. Nickel plays pivotal role in different kind of Heck reactions known such as intramolecular-, intermolecular-, reductive-Heck type reaction producing mainly carbocycles and hetero cycles of biological significance. Carbocyclization or hetero-cyclization reaction occurred under optimized reaction conditions developed and come up with the formation of various structural building blocks of naturally occurring compounds. Via reductive Heck cyclization large membered ring of carbo-or hetero-cyclic system was formed which performed key role as building blocks in pharmaceutical synthesis and bioactive molecule formation. Intermolecular Heck type reactions were comparatively more explored. Silyl-Heck, carbonyl-Heck, and other miscellaneous type reactions were covered up through nickel-catalyzed intermolecular Heck reaction. Asymmetric versions of Heck-coupling reactions are also reported to proceed even with unactivated alkenes, offering molecules having quaternary stereogenic center in a regio-and enantioselective manner. This manuscript intends to cover these entire concepts.

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Highly active homoleptic nickel(II) bis-N-heterocyclic carbene catalyst for Suzuki–Miyaura and Heck cross-coupling reactions

Cited by 10 publications

References 24 publications

Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

Intramolecular CH‐Hydrogen Bonding During the Dissociation of the Oxaphosphetane Intermediate Facilitates Z/E‐Selectivity in Wittig Olefination

Emerging Nickel Catalysis in Heck Reactions: Recent Developments

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