Cross-coupling Of Aryl Halides Research Articles

ChemInform Abstract: Gold‐Catalyzed Direct Arylation

AbstractReview: 43 refs.

Porous Chitosan Microspheres Supported-palladium Catalyst for the C–N Cross-coupling of Aryl Halides with Secondary Amines

Porous chitosan microspheres-supported palladium catalysed the amination of aryl halides with a wide variety of secondary amines to yield the corresponding cross-coupling products under aerobic conditions. Both aryl bromides and iodides gave good to excellent yields of N,N-disubstituted anilines. The procedure can tolerate common functional groups such as chloro, methoxyl and nitro. The heterogeneous catalysis is efficienct and the catalyst could be recycled seven times without obvious decreased conversion.

Room temperature Ullmann type C–O and C–S cross coupling of aryl halides with phenol/thiophenol catalyzed by CuO nanoparticles

C–O/C–S cross coupling of aryl halides with phenol or thiophenol was studied under ligand-free condition at room temperature over CuO nanocatalyst. The scope of the reaction was extended to various aryl halides and substituted phenols under optimized condition. In general, efficient, selective, and reusable heterogeneous nano CuO catalytic system has been developed for room temperature C–O and C–S Ullmann type cross coupling reactions.

Recent Advances of Modern Protocol for C-C Bonds—The Suzuki Cross-Coupling

Over the past 20 years, small molecule solid phase synthesis has become a powerful tool in the discovery of novel molecular materials. In the development of organic chemistry, the carbon-carbon bond formation has always been one of the most useful and fundamental reaction. The current review summarizes recent developments in metal-catalyzed coupling reactions. The following method is discussed in detail—the cross-coupling of aryl halides with aryl boronic acids (the Suzuki coupling), and the others C-C bond formation reactions as the palladium-catalyzed reaction between an aryl and (or) alkyl halide and a vinyl functionality (the Heck reaction); and the palladium-catalyzed cross-coupling reaction of organostannyl reagents with a variety of organic electrophiles (the Stille reaction)—are mentioned.

Preparation of carbon nanotube-supported α-Fe2O3@CuO nanocomposite: a highly efficient and magnetically separable catalyst in cross-coupling of aryl halides with phenols

Herein, we introduce the first magnetic CuO nanoparticles based on carbon nanotubes as a highly intriguing magnetic catalyst in Ullmann-type coupling of aryl halides with phenols. Two facile procedures were used for the preparation of this magnetically separable catalytic system. Having been treated with FeSO4 and then H2O2, nanotubes accommodated the resulting iron hydroxides on the walls. The resulting nanocomposite was then exposed to argon atmosphere at 450 °C giving rise to a carbon nanotube-supported α-Fe2O3 compound. Ultimately, copper acetate was hydrolysed in the presence of CNT supported α-Fe2O3 at 100 °C and our novel catalyst was gained. Some spectroscopic and microscopic techniques such as Infrared spectroscopy (IR), X-ray diffraction spectroscopy (XRD), Vibrational sample magnetometry (VSM), Brunauer–Emmett–Teller (BET), Barrett–Joyner–Halenda (BJH), Inductively coupled plasma (ICP), Scanning electron microscopy (SEM) and Transmission electron microscopy (TEM) corroborated the structure of the catalyst. The catalyst synthesized showed good activity in C–O cross coupling reactions affording the highest rate of completion. Magnetic feature of the catalyst helped facile separation of it from the reaction medium. The catalyst could also be reused up to six times without any loss of its activity.

ChemInform Abstract: [NiCl2(dppp)]‐Catalyzed Cross‐Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine.

We present a general approach to C?P bond formation through the cross-coupling of aryl halides with a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane by using [NiCl2(dppp)] as catalyst (dppp=1,3-bis(diphenylphosphino)propane). This catalyst system displays a broad applicability that is capable of catalyzing the cross-coupling of aryl bromides, particularly a range of unreactive aryl chlorides, with various types of phosphorus substrates, such as a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane. Consequently, the synthesis of valuable phosphonates, phosphine oxides, and phosphanes can be achieved with one catalyst system. Moreover, the reaction proceeds not only at a much lower temperature (100120?degrees C) relative to the classic Arbuzov reaction (ca. 160220?degrees C), but also without the need of external reductants and supporting ligands. In addition, owing to the relatively mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Finally, a brief mechanistic study revealed that by using [NiCl2(dppp)] as a catalyst, the NiII center could be readily reduced in situ to Ni0 by the phosphorus substrates due to the influence of the dppp ligand, thereby facilitating the oxidative addition of aryl halides to a Ni0 center. This step is the key to bringing the reaction into the catalytic cycle.

NiCl2(dppp)]‐Catalyzed Cross‐Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine

We present a general approach to C-P bond formation through the cross-coupling of aryl halides with a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane by using [NiCl(2) (dppp)] as catalyst (dppp=1,3-bis(diphenylphosphino)propane). This catalyst system displays a broad applicability that is capable of catalyzing the cross-coupling of aryl bromides, particularly a range of unreactive aryl chlorides, with various types of phosphorus substrates, such as a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane. Consequently, the synthesis of valuable phosphonates, phosphine oxides, and phosphanes can be achieved with one catalyst system. Moreover, the reaction proceeds not only at a much lower temperature (100-120 °C) relative to the classic Arbuzov reaction (ca. 160-220 °C), but also without the need of external reductants and supporting ligands. In addition, owing to the relatively mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Finally, a brief mechanistic study revealed that by using [NiCl(2) (dppp)] as a catalyst, the Ni(II) center could be readily reduced in situ to Ni(0) by the phosphorus substrates due to the influence of the dppp ligand, thereby facilitating the oxidative addition of aryl halides to a Ni(0) center. This step is the key to bringing the reaction into the catalytic cycle.

Application of a Nickel-Bispidine Complex as Pre-Catalyst for C(sp 2)–C(sp 3) Bond Formations

In the present study, the nickel-catalyzed cross coupling of aryl halides with benzyl zinc bromides or dialkyl zinc reagents to create C(sp 2)–C(sp 3) bonds has been explored. As pre-catalyst the well-defined and easy-accessible (bispidine)Ni(NO3)2 complex has been applied. After investigation of different reaction parameters a broad scope of C(sp 2)–C(sp 3) bond formations were feasible under mild reaction conditions. .

Ni-Catalyzed Cross-Coupling of Aryl Halides with Diphenylphosphine Oxide

Ni-Catalyzed Cross-Coupling of Aryl Halides with Diphenylphosphine Oxide

Ni(II)/Zn Catalyzed Reductive Coupling of Aryl Halides with Diphenylphosphine Oxide in Water

P-Arylation in water has been developed via cross-coupling of aryl halides with diphenylphosphine oxide (Ph(2)P(O)H) and (R(P))-(-)-menthyl benzylphosphinate catalyzed by NiCl(2)·6H(2)O/Zn under relatively mild conditions.

触媒的芳香族トリフルオロメチル化反応：最近の進展

Trifluoromethylated aromatic compounds are the substances of considerable interest in various industrial fields. The high lipophilicity, strong electron-withdrawing ability, and charasteristic size of trifluoromethyl group are key influences in biologically active molecules. Due to these attractive properties, the benzotrifluoride structural motifs have been widely employed in the design of pharmaceuticals, agrochemicals, dyes, liquid crystals, and polymers. Therefore, the development of highly efficient methodologies for aromatic trifluoromethylation is of significant importance for wide fields of science and technology. Recently, a great deal of attention has been paid to transition metal-catalyzed protocols to introduce trifluoromethyl groups into aromatic rings selectively. This review outlines the successful examples on catalytic aromatic trifluoromethylation, such as electrophilic and radical trifluoromethylation of aromatic compounds, cross-coupling of aryl halides with CF3Cu reagents, cross-coupling of aromatic halides with nucleophilic trifluoromethylation agents catalyzed by copper and palladium complexes, and catalytic oxidative cross-coupling to give trifluoromethylated aromatics effectively.

Recyclable NHC-Ni Complex Immobilized on Magnetite/Silica Nanoparticles for C-S Cross-Coupling of Aryl Halides with Thiols

A new type of magnetite/silica nanoparticle-supported N-heterocyclic carbene nickel catalyst (Mag-NHC-Ni) was developed from imidazolium with N-picolyl moieties and used as an efficient catalyst in the C-S coupling of various aryl halides with thiols. Moreover, the catalyst was easily recovered from the reaction mixture by simple filtration and recycled with almost consistent activity.

ChemInform Abstract: Directed ortho-Metalation - Suzuki Cross Coupling Connections. Convenient Regiospecific Routes to Functionalized m- and p-Teraryls and m-Quinquearyls.

Abstract Rapid access to a variety of substituted m- and p- teraryls and m- quinquearyls (Table) via Pd-catalyzed, one-pot, sequential and 1:2 cross coupling of aryl halides with aryl boronic acids, both available by metal-halogen exchange or directed ortho metalation tactics, is described.

Nano Indium Oxide as a Recyclable Catalyst for C−S Cross-Coupling of Thiols with Aryl Halides under Ligand Free conditions

An efficient ligand-free C-S cross-coupling of aryl halides with aromatic/alkyl thiols has been developed using a catalytic amount of nanocrystalline indium oxide as a recyclable catalyst with KOH as the base in DMSO at 135 degrees C. A variety of aryl sulfides can be synthesized in excellent yields utilizing this protocol.

Indium-Catalyzed C−S Cross-Coupling of Aryl Halides with Thiols

Indium-catalyzed C-S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)(3) (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 degrees C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.

Palladium on Carbon-Catalyzed Cross-Coupling of Aryl Halides with Potassium p-Tolyltrifluoroborate in Air

Palladium supported on carbon (Pd/C) has been shown to be an effective catalyst for the cross-coupling of potassium p-tolyltrifluoroborate with a variety of aryl bromides and iodides. Yields ranging from moderate to good were obtained using Pd/C in ethanol/water mixtures with potassium carbonate as base at 50 °C under an air atmosphere.

ChemInform Abstract: Efficient Iridium‐Catalyzed C—H Functionalization/Silylation of Heteroarenes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Efficient Iridium‐Catalyzed CH Functionalization/Silylation of Heteroarenes

As a consequence of their unique chemical, physical and biological properties, silyl-substituted arenes have attracted wide interest from the synthetic,[1] material science,[2] and pharmaceutical sectors.[3] Traditionally, silyl substituents have been introduced via addition of aryl lithium or magnesium reagents to silicon electrophiles, although this often necessitates the use of protecting groups.[4] Consequently, transition metal catalyzed cross couplings of aryl halides with disilanes or hydrosilanes have grown in popularity, especially if base-or nucleophile-sensitive functionality are present.[5] More recently, direct C-H functionalization[6] has emerged as a conceptually and economically attractive alternative for the direct silylation of arenes. It is evident, however, that challenges remain and the general utility of this strategy is restricted in many instances by, inter alia, (1) poor regioselectivity, (2) stringent structural requirements, (3) noncommercial/expensive reagents, (4) harsh reaction conditions (typically 120°–200°C), and/or (5) impractical ratios of arene to silicon reagent (10:1 to 60:1).[7–9] Herein, we report an efficient, regioselective protocol for the bipyridine-ligated, iridium-catalyzed[9] C-H functionalization/silyation of a wide variety of heteroarenes under comparatively mild conditions. Importantly, the reaction does not require protection of N-H groups and uses only a small excess (3 equiv) of inexpensive triethylsilane (eq 1).

Sequential Ni-Catalyzed Borylation and Cross-Coupling of Aryl Halides via in Situ Prepared Neopentylglycolborane

A procedure for NiCl(2)(dppp)-catalyzed pinacolborylation and neopentylglycolborylation that utilizes in situ prepared inexpensive pinacolborane and neopentylglycolborane is reported. The scope of this reaction was demonstrated with a variety of aryl bromides and iodides. The resulting aryl neopentylglycolboronic esters undergo a NiCl(2)(dppe)-catalyzed cross-coupling with aryl halides, resulting in an extremely efficient and cost-effective method for the synthesis of functional biaryls, dendritic building blocks, and other complex architectures.

ChemInform Abstract: Efficient Synthesis of Sterically Crowded Biaryls by Palladium—Phosphinous Acid Catalyzed Cross‐Coupling of Aryl Halides and Aryl Grignards.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.