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1.
Iron‐catalyzed cross‐coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents
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An Fe(III)‐catalyzed cross‐coupling of N‐heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The reaction proceeds at ?20°C to room temperature with short reaction time (15–30 min.), and the corresponding products are obtained with moderate to high yields. In particular, low‐cost and abundantly available FeCl3 or Fe(acetylacetonate)3 catalyze the reaction without other special ligands. All tested N‐heteroaromatic tosylates that are available including pyridine and pyrimidine derivatives were subject to the reaction, resulting in the expected products. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
2.
Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions
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In the presence of amino acids as environmentally friendly ligands, CuI‐catalyzed Sonogashira cross‐coupling of various aryl halides with phenylacetylene was conducted to afford the corresponding internal alkynes. l ‐Methionine was found to be useful for this palladium‐free and amine‐free coupling reaction. It was also found that the solvent system plays an important role in this reaction, and significantly affects the product formation and reaction rate. Sonogashira coupling of aryl iodides and aryl bromides in dimethylsulfoxide or dimethylformamide gave the coupled products in good to excellent yields. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
3.
《应用有机金属化学》2017,31(11)
A semi‐synthetic method has been developed for the synthesis of aminoarylbenzosuberenes (AABs) from naturally occurring himachalenes, an isomeric mixture of sesquiterpenes present in Cedrus deodara oil. Polymer‐stabilized Pd(0) nanoparticle‐catalysed Suzuki–Miyaura cross‐coupling reaction of aminovinyl bromide‐substituted benzosuberenes has been adopted for AAB synthesis. The catalyst performed well with different amine substituents, and was recycled up to five times. The synthesis of such arylated benzosuberene class of compounds from natural precursors following semi‐synthetic approaches could provide an attractive alternative method with reduced number of steps. 相似文献
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We present here the first synthesis and application to Sonogashira reaction of pyridine‐bis(ferrocene‐isoxazole) Pd(II) complex 5 , prepared from 2,6‐bis‐(5‐ferrocenylisoxazole‐3‐yl)pyridine. Under copper‐ and phosphine‐free conditions, the stable complex 5 efficiently catalyzed the cross‐coupling of aryl halides with terminal alkynes in DMF–H2O with TBAB as an additive, hexahydropyridine as base and affording internal arylated alkynes in moderate to excellent yields. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
5.
TMEDA in Iron‐Catalyzed Kumada Coupling: Amine Adduct versus Homoleptic “ate” Complex Formation
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Prof. Dr. Robin B. Bedford Dr. Peter B. Brenner Dr. Emma Carter Paul M. Cogswell Dr. Mairi F. Haddow Prof. Dr. Jeremy N. Harvey Prof. Dr. Damien M. Murphy Joshua Nunn Dr. Christopher H. Woodall 《Angewandte Chemie (International ed. in English)》2014,53(7):1804-1808
The reactions of iron chlorides with mesityl Grignard reagents and tetramethylethylenediamine (TMEDA) under catalytically relevant conditions tend to yield the homoleptic “ate” complex [Fe(mes)3]? (mes=mesityl) rather than adducts of the diamine, and it is this ate complex that accounts for the catalytic activity. Both [Fe(mes)3]? and the related complex [Fe(Bn)3]? (Bn=benzyl) react faster with representative electrophiles than the equivalent neutral [FeR2(TMEDA)] complexes. FeI species are observed under catalytically relevant conditions with both benzyl and smaller aryl Grignard reagents. The X‐ray structures of [Fe(Bn)3]? and [Fe(Bn)4]? were determined; [Fe(Bn)4]? is the first homoleptic σ‐hydrocarbyl FeIII complex that has been structurally characterized. 相似文献
6.
Iminophosphine palladium(II) complexes: synthesis,characterization, and application in Heck cross‐coupling reaction of aryl bromides
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Palladium(II) complexes containing phosphorus and nitrogen donor atoms (iminophosphine), dichlorido{N‐[2‐(diphenylphosphino)benzylidene]‐2‐trifluoromethylaniline}palladium(II) 1 , dichlorido{N‐[2‐(diphenylphosphino)benzylidene]‐3‐trifluoromethylaniline}palladium(II) 2 , dichlorido{N‐[2‐(diphenylphosphino)benzylidene]‐2‐methylaniline}palladium(II) 3 , dichlorido{N‐[2‐(diphenylphosphino)benzylidene]‐3‐methylaniline}palladium(II) 4 have been successfully synthesized and fully characterized by FT‐IR and NMR (1H, 31P, 19F, and 13C) spectroscopy techniques. These complexes were first step tested in the reaction of bromobenzene and styrene to determine the optimal coupling reaction conditions and then successfully applied as catalysts for Heck cross‐coupling reactions of activated and deactivated aryl bromides with styrene derivatives and several acrylates. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
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A highly efficient and mild palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides and aryl bromides for the selective synthesis of unsymmetrical biaryls has been developed. This methodology has the advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provide rapid access to biaryls derivatives. In this protocol, abundant and stable aryl bromides serve as the aryl sources by coupling reaction of the aryl group generated from arylsulfonyl hydrazides via in situ release of nitrogen and sulfur dioxide. No external oxidants or acids are needed for this kind of transformation. 相似文献
8.
Xue‐Xin Feng Zhen Wu Qing‐Dong Wang Bing‐Zhi Chen Weidong Rao Jin‐Ming Yang Zhi‐Liang Shen 《应用有机金属化学》2019,33(9)
A catalytic amount of cesium carbonate (10 mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus‐generated alkyl indium reagents could readily undergo palladium‐catalyzed cross‐coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups. 相似文献
9.
The bio‐based chemical ethyl lactate (EL) has been discovered to be an excellent medium for the Glaser‐type homo‐ and cross‐coupling reactions of terminal alkynes. Good to excellent yields of conjugate diynes have been obtained under ligand‐free and mild heating conditions in the presence of CuI and molecular oxygen. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
10.
C–N cross‐coupling reaction catalysed by efficient and reusable CuO/SiO2 nanoparticles under ligand‐free conditions
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Nanometric copper oxide supported on silica has been found to be a highly efficient and reusable catalyst for the C–N cross‐coupling reaction of amines with aryl halides under ligand‐free conditions. Various arylamines with different substituted groups can be synthesized in moderate to good yields. The catalyst can be recycled at least five times without obvious loss in catalytic activity. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
11.
A versatile method for the synthesis of diaryl and alkyl aryl ketones via palladium‐catalysed cross‐coupling reaction of arylboronic acids with acyl chlorides
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An efficient catalytic system using 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride and PdCl2 was developed for the cross‐coupling reaction of arylboronic acids with acyl chlorides. The catalytic amount of this homogeneous catalytic system affords the corresponding diaryl and alkyl aryl ketones in good to excellent yields under mild reaction conditions. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
12.
The Suzuki reaction of primary alkylboronic acids with alkenyl halides proceeds nicely using the air‐stable catalyst PdCl(C3H5)(dppb), Cs2CO3 as base and toluene or xylene as solvent. A minor effect of the substituent position of the alkenyl bromide was observed. Quite similar yields were observed in the presence of α‐ or β‐substituted alkenyl bromides such as 2‐bromobut‐1‐ene or 1‐bromo‐2‐methylprop‐1‐ene with this catalyst. This reaction proceeded with a variety of alkylboronic acids such as 2‐phenylethylboronic acid or n‐octylboronic acid. Lower yields of coupling products were obtained in the presence of an alkenyl chloride. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
13.
Copper‐catalyzed C(sp2)–C(sp) Sonogashira‐type cross‐coupling reactions accelerated by polycyclic aromatic hydrocarbons
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Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf)2/pyrene system was subsequently employed to synthesize phenylacetylene‐based fluorescent compounds. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
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The Suzuki cross‐coupling reaction of various bromine‐containing substrates and phenylboronic acid in toluene at 90 °C on a Pd(AcO)2Py2 catalyst supported on an Mg? Al hydrotalcite, using K2CO3 as the base, was studied. The conversion and selectivity results obtained for many of the substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The reactions of aryl polybromides and phenylboronic acid gave the corresponding polyaromatic compounds in variable yields depending on the particular substrate. Arylation occurred in a consecutive manner by substitution of the different Br atoms. ICP‐MS measurements of the palladium content of the catalyst performed prior to and after the reaction revealed that part of the metal is incorporated into the bulk solution; therefore, the catalytic process is not purely heterogeneous. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
17.
《应用有机金属化学》2017,31(8)
A series of ionic iron(III) complexes of general formula [HLn ][FeX4] (HL1 = 1,3‐dibenzylbenzimidazolium cation, X = Cl, 1 ; HL1, X = Br, 2 ; HL2 = 1,3‐dibutylbenzimidazolium cation, X = Br, 3 ; HL3 = 1,3‐bis(diphenylmethyl)benzimidazolium cation, X = Br, 4 ) were easily prepared in high yields by the direct reaction of FeX3 with 1 equiv. of [HLn ]X under mild conditions. All of them were characterized using elemental analysis, Raman spectroscopy and electrospray ionization mass spectrometry, and X‐ray crystallography for 1 and 4 . In the presence of magnesium turnings and LiCl, these air‐ and moisture‐insensitive complexes showed high catalytic activities in direct cross‐couplings of aryl phosphates with primary and secondary alkyl bromides with broad substrate scope, wherein complex 4 was the most effective. 相似文献
18.
Synthesis,characterization and application of graphene palladium porphyrin as a nanocatalyst for the coupling reactions such as: Suzuki‐Miyaura and Mizoroki‐Heck
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The palladium(II)‐coordinated 5,10,15,20‐tetrakis‐(4‐hexyloxyphenyl)‐porphyrin as a macrocyclic palladium complex was covalently grafted to the surface of graphene oxide (denoted as GO‐CPTMS@Pd‐TKHPP). GO‐CPTMS@Pd‐TKHPP was characterized using microscopic and spectroscopic techniques for confirmation of functionalization. The synthesized catalyst was checked in the Suzuki‐Miyaura and the Mizoroki‐Heck coupling reactions. The catalyst is very easy to handle, environmentally safe and economical. Also, this catalytic system shows high catalytic activity and the yields of the products are excellent. Moreover, the suggested catalyst was reusable for five runs with no significant decrease in catalytic activity. 相似文献
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《应用有机金属化学》2017,31(6)
A novel heterogeneous Pd catalyst was synthesized by anchoring Pd(II) onto 4′‐(4‐hydroxyphenyl)‐2,2′:6′,2″‐terpyridine‐coated Fe3O4 (FMNPs@TPy‐Pd). This catalyst has been demonstrated for the first time as a recoverable and reusable heterogeneous nanocatalyst in Suzuki and Heck cross‐coupling reactions. The catalyst is very easy to handle and is environmentally safe and economical. FMNPs@TPy‐Pd was characterized using transmission and scanning electron microscopies, X‐ray diffraction, and Fourier transform infrared and energy‐dispersive X‐ray spectroscopies. 相似文献