Employing Water as the Hydride Source in Synthesis: A Case Study of Diboron Mediated Alkyne Hydroarylation

Rao, Santhosh; Joy, Muthipeedika Nibin; Prabhu, Kandikere Ramaiah

doi:10.1021/acs.joc.8b01965

Cited by 29 publications

(9 citation statements)

References 40 publications

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“…m/z (%): 301 (M + ). The data is consistent with the literature(Rao et al, 2018). colorless oil (74% yield); 1 H NMR(400 MHz, CDCl 3 ) δ 7.36-7.28 (m, 8H), 7.22-7.16 (m, 4H), 7.04 (d, J = 8.1 Hz, 2H), 6.95 (s, 1H), 3.01 (s, 6H) ppm; 13 C NMR (100 MHz, CDCl 3 ) δ 171.…”

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confidence: 92%

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Suzuki-Miyaura Coupling Enabled by Aryl to Vinyl 1,4-Palladium Migration

Han

et al. 2020

iScience

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The Suzuki-Miyaura coupling is a fundamentally important transformation in modern organic synthesis. The development of new reaction modes for new chemical accessibility and higher synthetic efficiency is still the consistent pursuance in this field. An efficient Suzuki-Miyaura coupling enabled by a controllable 1,4-palladium migration was realized to afford stereodefined multisubstituted olefins and 1,3-dienes. The reaction exhibits remarkable broad substrate scope, excellent functional-group tolerance, versatile conversion with obtained products, and easy scalability. The practicality of this method is highlighted by the aggregation-induced emission feature of the produced olefins and 1,3-dienes, as well as the capability of affording geometric isomer pairs with a marked difference on photoluminescent quantum yield values.

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confidence: 92%

“…4-(2,2-diphenylvinyl)benzonitrile (3ah), white solid (83% yield); 1 H NMR (400 MHz, CDCl 3 ) δ 7.39 (d, J = 8.3 Hz, 2H), 7.37-7.30 (m, 8H), 7.17 (s, 2H), 7.08 (d, J = 8.4 Hz, 2H), 6.94 (s, 1H) ppm; EI-MS m/z (%): 281(M + ). The data is consistent with the literature(Rao et al, 2018). m/z (%): 301 (M + ).…”

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confidence: 92%

Suzuki-Miyaura Coupling Enabled by Aryl to Vinyl 1,4-Palladium Migration

Han

et al. 2020

iScience

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“…This is a critical requirement for the synthesis of nearly any functional alkene. Various transition metals including Cr, Mn, Fe, Co, Ni, Cu, Rh, and Pd have all been used as catalysts for alkene synthesis in this fashion. Frequently, an organometallic reagent containing Li, B, Mg, Zn, or Sn is added to the alkyne, although other reagents including carbon dioxide and organohalides can undergo addition as well if a stoichiometric reductant is included.…”

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confidence: 99%

Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water

et al. 2019

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An operationally simple nickel-catalyzed hydroarylation reaction for alkynes is described. This threecomponent coupling reaction utilizes commercially available alkynes and aryl bromides, along with water and Zn. An airstable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not commercially available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data and a preliminary substrate scope, complementary experiments including deuterium labeling studies are used to provide a tentative catalytic mechanism. We believe this report should inspire and inform other Ni-catalyzed carbofunctionalization reactions.

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“…The transition-metal-catalyzed conjugate addition of organoboron reagents to unsaturated alkenes and alkynes is one of the most useful synthetic strategies to form a C–C bond over the past several decades . Among them, the palladium-catalyzed addition/cyclization reaction involving organoborons and alkynes provides one of the most straightforward pathways for the formation of carbocycles and heterocycles .…”

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confidence: 99%