Di-t-butyl(ferrocenylmethyl)phosphine: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

Sliger, Michael D.; Broker, Grant A.; Griffin, Scott T.; Rogers, Robin D.; Shaughnessy, Kevin H.

doi:10.1016/j.jorganchem.2004.12.022

Cited by 21 publications

(11 citation statements)

References 51 publications

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“…26 Similar results have been previously reported for other catalytic systems of Pd(II)/phosphines/p-TsOH. 27,28 In agreement with other Pd-catalytic systems containing monodentate phosphines, [3][4][5]18 our system show favorable regioselectivity to form methyl-2-phenylpropanoate (Table 1).…”

Section: -Results and Discussionsupporting

confidence: 89%

“…This situation contrast with the remarkably success of ferrocenyl phosphines for palladium catalyzed C-C, C-N and C-O bond-forming cross coupling. [17][18][19] Recently, Claver et al have demonstrated that ferrocenylphosphoetane ligand produces high regioselectivity (99:1, b:l) but low conversion. 20 According to our acknowledge, no others cyclopentadienylphosphines …”

Section: -Introductionmentioning

confidence: 99%

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Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Zúñiga¹,

Sierra

Oyarzo

et al. 2012

J. Chil. Chem. Soc.

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The palladium-catalyzed methoxycarbonylation of vinylarenes has been investigated for the first time using phosphinocyrhetrene [(η 5 -C 5 H 4 PPh 2 )Re(CO) 3 ] a non-metallocenic organometallic ligand. The catalytic system trans- [(η 5 -C 5 H 4 PPh 2 )Re(CO) 3 ]PdCl 2 (NCMe)/PPh 3 (1:2 ratio), carbon monoxide and methanol, in the presence of HCl as acidic promoter, showed good catalytic activity, excellent regioselectivity to the branched products and chemoselectivity up to 94%.Keywords: Methoxycarbonylation, phosphinocyrhetrene ligand, vinylarenes. 1.-INTRODUCTIONPalladium-catalyzed hydroesterification reaction (Reppe carbonylation) is a powerful synthetic strategy for the preparation of linear and branched esters from easily available unsaturated substrates.1,2 It has been established that the regioselectivity of carboxylation products is strongly dependent on the ligands bound to a transition metal and the reaction conditions. The most common catalytic system involve Pd(II) and mono-and bidentate aromatic phosphines. Catalysts containing bidentate diphosphine ligands have been more frequently used for this reaction, but they have the disadvantage to produce branched product in low regio-and enantioselectivity, although a few successful examples have been reported recently.3-7 Several chelating diphosphines have been extensively studied, particularly interesting are those containing metallocenic fragments, for instance, palladium(II) complexes with 1,1-bis(diphenylphosphino)ferrocene (dppf), 1,1-bis(diphenylphosphino) octamethylferrocene (dppomf), 1,1-bis(diphenyl-phosphino)ruthenocene (dppr), and bis(diphenylphosphino)osmocene (dppo) have proven to catalyze the methoxycarbonylation of ethylene and styrene, showing high selectivity to the linear ester. [8][9][10][11][12][13] Gusev et. al.14 have stated that the steric and electronic properties of these metallocenes carrying phosphine ligands, should form M-Pd (M=Fe, Ru and Os) bonds throughout the catalytic cycle, favoring the formation of the linear product. Recently, it has been established, that products with high linearity can be achieved by using chelating systems, in which the diphosphines promote the most favored cis-coordinated complexes. 15On the other hand, palladium complexes containing monodentate phosphine ligands have also been of interest for the catalyzed-hydroesterification reactions since their use provides high regioselectivity to the branched ester but the enantioselectivity is usually low. Despite the large number of monophosphine containing ferrocene described in literature 16 only few of them have been used in hydroesterification reactions. This situation contrast with the remarkably success of ferrocenyl phosphines for palladium catalyzed C-C, C-N and C-O bond-forming cross coupling. 2.-EXPERIMENTAL SECTIONAll experiments were performed under nitrogen using standard Schlenck techniques. Organic solvents were purified by standard methods. All chemicals were reagent-grade and used as received unless otherwise specified styrene...

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Section: -Results and Discussionsupporting

confidence: 89%

Section: -Introductionmentioning

confidence: 99%

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Zúñiga¹,

Sierra

Oyarzo

et al. 2012

J. Chil. Chem. Soc.

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“…Recently, researchers are giving more attention regarding cross-coupling reaction due to its ability in the formation of C-C bonds with excellent yield. Since then, a large number of catalytic systems have been proposed to reduce the weaknesses associated with cross-coupling reaction, especially the involvement of phosphine as ligands in palladium catalyzed crosscoupling reactions [7][8].…”

Section: Introductionmentioning

confidence: 99%

An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest

Khairul

Shariff

Rahamathullah

et al. 2017

MST

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The synthesis and utilization of C-C bonds formation are concerned about the key steps for the building of several conducting molecular electronics involving many asymmetric catalysts approached, which is an essential task that most researchers would ignore in preparing these materials to enhance the production yield of cross-coupling materials. Despite the enormous progress, there still remains a great demand for economic and practicable cross-coupling processes involving ultra-low catalyst loadings with high turnover numbers due to the employment of conventional metal catalyst. Thus, there has been an excessive interest to cultivate non-phosphine palladium catalysts for excellent achievement of activity, stability, and substrate tolerance which permit the coupling reactions to be conducted under mild reaction condition at ambient atmosphere. In this contribution, N-(4-nitrophenylcarbamothioyl)-N'-(4-methylbenzoyl) thiourea (LT1) and its metal complex of MLT1 featuring Pd (II) have been successfully characterised via typical spectroscopic methods namely; Infrared (IR) spectroscopy, Ultraviolet-visible (UV-Vis) spectroscopy, CHNS elemental analysis, and Nuclear Magnetic Resonance ( 1 H and 13 C NMR). In turn, catalytic studies of palladium catalyst (MLT1) were tested for its homogenous catalytic activity in Heck cross-coupling reaction. The reaction was monitored by Gas Chromatography-Flame Ionisation Detector (GC-FID). Results reveal that MLT1 exhibits 100% of conversion starting material into a cross-coupling product, which was alkene-based compound. Abstrak Palladium-Tiourea Yang Efisien Sebagai Katalis Reaksi Gandengan Silang Heck Untuk Molekul Elektronik.Sintesis dan penggunaan pembentukan ikatan C-C perlu diperhatikan sebagai langkah utama untuk membina beberapa molekul elektronik terkonduksi yang melibatkan banyak katalis-katalis asimetris, yang merupakan tugas yang sering diabaikan oleh kebanyakan peneliti dalam menyediakan bahan-bahan ini untuk meningkatkan pengeluaran hasil bahan gandengan silang. Meskipun telah banyak perkembangan dalam hal ini, masih ada permintaan yang tinggi untuk proses gandengan silang yang lebih ekonomis dan praktis yang hanya melibatkan pembekalan katalis yang sangat rendah dengan hasil perolehan yang tinggi dengan penggunaan katalis logam biasa. Oleh karena itu, terdapat banyak kepentingan untuk menghasilkan katalis paladium tanpa fosfina untuk pencapaian yang cemerlang dari segi aktivitas, kestabilan dan toleransi substrat yang membenarkan reaksi gandengan silang yang dijalankan dalam keadaan reaksi sederhana pada keadaan atmosfer tertentu. Dalam kajian ini, N-(4-nitrofenilcarbamotionil)-N'-(4-metilbenzoil) tiourea (LT1) dan kompleks logamnya yaitu MLT1 menampilkan Pd(II) telah berhasil dicirikan melalui kaidah spektroskopi yang biasa yaitu spektroskopi sinar inframerah (IR), spektroskopi Ultra-Lembayung Sinar Nampak (UV-Vis), analisis unsur CHNS dan Resonan Magnetik Nukleus ( 1 H dan 13 C NMR). Selanjutnya, tindak balas ini dipantau menggunakan Gas Chromatography-Fla...

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“…The heterobimetallic Re-Pd complex (CO) 3 Re(η 5 -C 5 H 4 PPh 2 )PdCl 2 (NCMe) I and the chelated complexes (η 5 -C 5 H 4 PPh 2 )(CO) 2 PR 3 Re-PdCl 2 (R = Me, II and R = OMe, III) were used as precatalyst for the Suzuki reaction. Complexes II and III containing a metal-metal bond were shown to be more efficient precatalyst for crosscoupling reaction of a wide range of aryl bromides electronically activated, unactivated and sterically hindered.…”

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confidence: 99%

“…An important part of these studies have been focused in the use of organometallic phosphines, mainly ferrocenylphosphines as a ligands, because the electron-rich metallocene helps to provide the electronic and steric characteristics that are often required to form a highly active catalyst [3][4][5].…”

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confidence: 99%

Suzuki cross-coupling of aryl bromides catalyzed by cyrhetrenylphosphine complexes of palladium (II)

Sierra

Zúñiga

Buono-Core

et al. 2011

Inorganic Chemistry Communications

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Di-t-butyl(ferrocenylmethyl)phosphine: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

Cited by 21 publications

References 51 publications

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest

Suzuki cross-coupling of aryl bromides catalyzed by cyrhetrenylphosphine complexes of palladium (II)

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