Redox chemistry of copper acetate binuclear complexes in acetic acid-methanol mixture as solvent

Toledo, Ivonne; Arancibia, María José; Andrade, Carlos; Crivelli, Irma

doi:10.1016/s0277-5387(97)00209-x

Cited by 14 publications

(7 citation statements)

References 12 publications

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“…After 24 hours, nitroalkene was consumed to give 7a in high yield. Therefore, copper trifluoroacetate is beneficial for oxidative annulation due to its higher oxidation potential, 25 which afforded a smooth aromatization of primary cycloadducts in mild conditions.…”

Section: Resultsmentioning

confidence: 99%

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

2022

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Section: Resultsmentioning

confidence: 99%

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

2022

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“…After 24 hours, nitroalkene was consumed to give 7a in high yield. Therefore, copper trifluoroacetate is beneficial for oxidative annulation due to its higher oxidation potential, 24 which afforded a smooth aromatization of primary cycloadducts in mild conditions.…”

Section: Resultsmentioning

confidence: 99%

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(II): efficient synthesis of [5,5]-annulated N-fused heterocycles

Motornov¹,

Tabolin²,

Ioffe³

2021

Preprint

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A facile synthesis of [5,5]-annulated N-fused heterocycles – pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via Cu(II)-mediated oxidative [3+2]-annulation between nitroalkenes and azolium ylides was developed. The reaction proceeds in mild conditions with copper (II) trifluoroacetate/2,6-lutidine system as a promoter. The method is applicable to a broad range of nitroalkenes and azolium salts, providing target N-fused heterocycles in moderate to good yields. In the case of α-fluoronitroalkenes unique fluorinated derivatives were accessed via this methodology.

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“…Also, using CuOAc gave no H/D exchange of toluene- d 8 (Table , entry 20), and the combination of CuOAc and 1a resulted in meta-selective H/D exchange with lower TOs (11(1) at 8 h) (Table , entry 21) compared to Cu(OAc) 2 . It remains unclear whether the observed H/D exchange of toluene- d 8 is facilitated by the CuOAc or Cu II that is potentially formed from the disproportionation of CuOAc under the reaction conditions. − …”

Section: Resultsmentioning

confidence: 99%

Effects of Additives on Catalytic Arene C–H Activation: Study of Rh Catalysts Supported by Bis-phosphine Pincer Ligands

Kong

Liu

et al. 2020

Organometallics

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Hydrogen−deuterium exchange (H/D exchange) is a method commonly used for studying catalytic activation of C−H(D) bonds by transition metal complexes. In this study, a series of additives were studied for H/D exchange of toluene-d 8 with acetic acid (HOAc) using ( R PNP)Rh(X) complexes (R = phosphine substituents including cyclohexyl, isopropyl, and tert-butyl; X = trifluoroacetate or acetate) as the precatalysts. Cu(OAc) 2 and AgOAc additives were found to benefit Rh-mediated C−H(D) activation of toluene with meta−para selectivity by facilitating the conversion to active ( R PNP)Rh species and stabilizing the Rh catalysts from decomposition to inactive Rh(s). In contrast, nonoxidizing Lewis acid additives, such as B(OMe) 3 or NaOAc, were not effective at facilitating Rh-catalyzed toluene C−H activation. The complexes ( R PNP)Rh III (H)(X) 2 and [( R PNP)Rh I (CO)][X] (X = TFA or OAc) were found to be intermediates of the catalytic the H/D exchange.

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Redox chemistry of copper acetate binuclear complexes in acetic acid-methanol mixture as solvent

Cited by 14 publications

References 12 publications

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(II): efficient synthesis of [5,5]-annulated N-fused heterocycles

Effects of Additives on Catalytic Arene C–H Activation: Study of Rh Catalysts Supported by Bis-phosphine Pincer Ligands

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