Cu(I) catalyzed dehydrogenative homo coupling of aromatic amines under simple and mild reaction conditions

Reddy, C. Bhupendra; Reddy, Sabbasani Rajasekhara; Naidu, S. Vasudeva

doi:10.1016/j.catcom.2014.06.025

Cited by 42 publications

(17 citation statements)

References 20 publications

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“…Previously, this transformation was achieved with stoichiometric amounts of oxidants [17] or by copper catalysis. [18] Electron-rich tetraarylhydrazines were reported to be unstable under thermal, photochemical, and acidic conditions. [19] In fact, the tetraarylhydrazines 6 proved to be much less stable than the 5,6-dihydrobenzo[c]cinnolines 5.…”

Section: Angewandte Chemiementioning

confidence: 99%

Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines

et al. 2016

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We describe iron-catalyzed intermolecular oxidative coupling reactions of diarylamines to form substituted 2,2'bis(arylamino)biaryl compounds, tetraarylhydrazines, and 5,6dihydrobenzo[c]cinnolines with the same hexadecafluorinated iron-phthalocyanine catalyst. The mild formation of CÀC or N À N bonds was controlled by the use of acidic or basic additives. In contrast to most iron-catalyzed dehydrogenative coupling reactions, ambient air could be used as the sole oxidant. Moreover, iron(III) chloride hexahydrate promoted a one-pot coupling and subsequent intramolecular dearomative coupling to give 10H-spiro[acridine-9,1'-cyclohexa-2',5'dien-4'-ones].

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Section: Angewandte Chemiementioning

confidence: 99%

Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines

et al. 2016

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“…Kajimoto et al showed that N–N coupling of the parent diphenylamine could be achieved under aerobic conditions with stoichiometric CuCl, 15 and Knölker recently described an Fe(phthalocyanin) catalyst for aerobic oxidative N–N coupling of diarylamines. 5h,16,17 The present reactions were conducted at room temperature in DCM with 10 mol% CuBr·DMS and 20 mol% DMAP. Several substrates underwent conversion to the corresponding tetrarylhydrazine in near-quantitative yield (cf.…”

mentioning

confidence: 99%

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

2018

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A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N-N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O, 60-80 °C) with a catalyst composed of CuBr·dimethylsulfide and N, N-dimethylaminopyridine. Reactions between carbazole and diarylamines show unusually selective cross-coupling, even with a 1:1 ratio of the two substrates. This behavior was found to arise from reversible formation of the tetraarylhydrazine. Formation of this species is kinetically favored, but cleavage of the N-N bond under the reaction conditions leads to selective formation of the thermodynamically favored cross-coupling product.

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“…In the earlier work by Reddy et al, homocoupling of simple and substituted aromatic amines at ambient temperature under mild conditions was reported [19][20] . Luminol is a basic aromatic amine with a phthalhydrazide group.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 2 was synthesized according to the procedure earlier reported by Reddy et al, [19][20] Accurately weighed Luminol (250 mg, 1.0 mmol) was taken in a dry 100 ml two necked round bottom flask followed by the addition of 4-dimethyl aminopyridine (DMAP) (150 mg, 1.2 mmol), cuprous bromide (14.3 mg, 0.10 mmol) and Azobisisobutyronitrile (AIBN) (50 mg, 0.3 mmol) under an inert atmosphere condition. To these contents, 3 ml of DMF was added.…”

Section: Synthesis Of Compoundmentioning

confidence: 99%

“…Reddy et al, have reported the synthesis of a series of symmetrical azobenzenes from various aromatic amines using Cu(I) catalyzed dehydrogenative homocoupling using mild reaction conditions. [19][20] The catalytic system employed was Cu(I)Br along with DMAP (Dimethylamino pyridine) and AIBN (Azobisisobutyronitrile). Luminol 1 is also basically an aromatic amine with a phthalhydrazide group.…”

Section: Introductionmentioning

confidence: 99%

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Green Chemiluminescence of Highly Fluorescent Symmetrical Azo-Based Luminol Derivative

Deepa¹,

Reddy²,

Rajendrakumar³

2018

Orient. J. Chem

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A symmetrical azo-based Luminol derivative 2 was synthesized using catalytic dehydrogenative coupling reaction procedure. This symmetrical molecule shows blue fluorescence in polar aprotic solvents (λ max = 450 nm). With an increase in aqueous content 2 was exhibiting aggregation caused fluorescence quenching (ACQ) with a red shift of 30 nm (λ max = 480 nm). Distinct emission features were observed for this molecule with a variation in the pH range. In basic medium, deprotonated form of 2 shows fluorescence quenching followed by enhancement of green chemiluminescence (λ max = 490 nm) with H 2 O 2 /Fe 3+ catalytic system. The fluorescence and chemiluminescent (CL) properties of 2 were compared with its parent luminol 1, The CL emission intensity of 2 was found to be about 16 times higher than that of 1. In addition, HOMO-LUMO energy gap for 2 was also calculated using density functional theory (DFT) studies.

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Cu(I) catalyzed dehydrogenative homo coupling of aromatic amines under simple and mild reaction conditions

Cited by 42 publications

References 20 publications

Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines

Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

Green Chemiluminescence of Highly Fluorescent Symmetrical Azo-Based Luminol Derivative

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