Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction

Hajipour, Abdol R.; Rafiee, Fatemeh

doi:10.1016/j.jorganchem.2011.03.023

Cited by 31 publications

(23 citation statements)

References 65 publications

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“…In continuation of our recent investigations on the synthesis and application of the palladium catalysts, [20][21][22][23][24][25][26] we now wish to report the extension of a complex of 1-benzyl-4-aza- [27] The reaction of [BeDABCO]Cl with PdCl 2 in a 1:1 ratio in acetone reflux gave the (BeDABCO) 2 Pd 2 Cl 6 complex (1). [28] The efficiency of this catalytic system was evaluated in a Hiyama cross coupling reaction under microwave irradiation.…”

Section: Resultsmentioning

confidence: 99%

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Hiyama cross‐coupling reaction catalyzed by a palladium salt of 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride under microwave irradiation

Hajipour

Rafiee

Najafi

2014

Applied Organom Chemis

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Section: Resultsmentioning

confidence: 99%

“…Aryl chlorides converted to corresponding products more slowly and with lower yields in comparison to the similar aryl iodides and bromides ( Table 2, entries [19][20][21][22]. The steric hindrance of the procedure was examined using 2-, 3-and 4-bromoacetophenone as hindered substituted aryls ( Table 2, entries [11][12][13].…”

Section: Resultsmentioning

confidence: 99%

Hiyama cross‐coupling reaction catalyzed by a palladium salt of 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride under microwave irradiation

Hajipour

Rafiee

Najafi

2014

Applied Organom Chemis

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“…The use of homogeneous metal catalysts in conjunction with microwave heating leads to increased lifetimes of the catalyst, saves time, and produces high yields of products with less by-product formation via thermal side-reactions. 22,23 In continuation of our recent investigations on the synthesis and applications of palladacycle catalysts in microwave assisted cross-coupling reactions, [24][25][26][27][28][29][30] we now report the extension of dimeric [Pd{C 6 H 2 (CH 2 CH 2 NH 2 )-(OMe) 2 -3,4}(l-Br)] 2 A suitable chemical production process utilizing palladium catalysis requires high catalyst productivity and activity. Also the availability and cost of catalysts and the price of the organic starting materials are of great importance for industrial processes.…”

Section: Introductionmentioning

confidence: 88%

Microwave-assisted Stille and Hiyama cross-coupling reactions catalyzed by ortho-palladated complexes of homoveratrylamine

Hajipour

Rafiee

2012

Tetrahedron Letters

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“…Products were identified by comparison of their FTIR and 1 H and 13 C NMR spectra with those reported in the literature. 39,52,[54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69] Copyright of Synlett is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use.…”

Section: Mizoroki-heck Reaction Of Aryl Halides With Olefins; Generalmentioning

confidence: 99%

A Robust, Moisture- and Air-Stable Phosphine Mono-Ylide Palladacycle Precatalyst: A Simple and Highly Efficient System for Mizoroki–Heck Reactions

Sabounchei

Ahmadi

Azizi

et al. 2013

Synlett

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A palladacycle phosphine mono-ylide complex was identified as an efficient catalyst system for the Mizoroki-Heck cross-coupling reactions of aromatic or aliphatic olefins with a variety of aryl bromides and chlorides, including those containing electron-donating or electron-withdrawing substituents. The reactions, which proceeded in moderate to excellent yields, required relatively low loadings of palladium (10 ppm) and were performed under aerobic conditions. High catalyst activities with turnover frequencies of up to 20,000 h -1 were observed at 130°C.The palladium-catalyzed arylation of olefins, known as the Heck cross-coupling reaction, is one of the most versatile tools for forming carbon-carbon bonds. 1-6 Tolerance to a wide spectrum of functional groups in both substrates makes this reaction very useful in total syntheses. Historically, palladium complexes with phosphine ligands have been widely used to catalyze these reactions. 7-10 The phosphine ligands act as stabilizers for catalytically active palladium(0) complexes that are generated in situ. Palladium complexes with bulky and strongly electrondonating trialkylphosphines are favored for carboncarbon coupling of aryl halides with styrene; 11,12 however, diphosphine ligands, because of their chelating effects, generally shows better coordination ability in stabilizing active palladium species in the catalytic cycle. Among the existing catalysts for these reactions, the most effective are homogeneous palladium-ligand systems. [13][14][15][16][17][18][19] The efficiency of a Heck reactions is greatly dependent on the reactivity of the palladacycle catalyst precursors. It is well established that palladacycle complexes containing phosphine ligands that combine both good donor strength and π-accepting capacity have high catalytic activities in Heck cross-coupling reactions. 20-22 Over the past ten years, we have studied phosphorus ylides and their palladium complexes, 23-28 and we have used some of these complexes in carbon-carbon coupling reactions. [29][30] Here, we describe the use of precatalyst 1 to promote the Mizoroki-Heck coupling reaction of aryl bromides or chlorides with olefins (Scheme 1). The reaction proceeds smoothly with deactivated aryl bromides or activated aryl chlorides and it gives good yields at low palladium loadings under aerobic conditions.The catalyst precursor 1 used for the Mizoroki-Heck cross-coupling reaction was prepared in high yield by reaction of 1-biphenyl-4-yl-2-[[(diphenylphosphino)-methyl](phenyl)phosphino]ethanone with dichloro(cyclooctadienyl)palladium in a 1:1 molar ratio at room temperature. 31The palladium-catalyzed Mizoroki-Heck reaction is among the most important carbon-carbon bond-forming processes for the vinylation of aryl or vinyl halides. As a result, considerable effort has been made to develop new and improved protocols for the Heck coupling reaction since the pivotal discovery of the reaction by Heck and Mizoroki in the early 1970s. [32][33][34][35] Many palladium phosphine complexes have been used as c...

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Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction

Cited by 31 publications

References 65 publications

Hiyama cross‐coupling reaction catalyzed by a palladium salt of 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride under microwave irradiation

Hiyama cross‐coupling reaction catalyzed by a palladium salt of 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride under microwave irradiation

Microwave-assisted Stille and Hiyama cross-coupling reactions catalyzed by ortho-palladated complexes of homoveratrylamine

A Robust, Moisture- and Air-Stable Phosphine Mono-Ylide Palladacycle Precatalyst: A Simple and Highly Efficient System for Mizoroki–Heck Reactions

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