Advances in the Heck chemistry of aryl bromides and chlorides

Whitcombe, Nicole J.; Hii, King Kuok; Gibson, Susan E.

doi:10.1016/s0040-4020(01)00665-2

Cited by 592 publications

(228 citation statements)

References 110 publications

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“…This section describes few reviews that draw attention to future challenges in this area by highlighting advances concerning Heck reactions using aryl bromides and chlorides. A review by Whitecombe and others [24] discuss the development of catalytic systems that can activate unreactive aryl halide Farina [23] has discussed the problems associated like scope, purity, impurity profile, throughput and time for developing high-turnover catalysts for the cross-coupling and Heck reactions. Numerous examples are given to illustrate the developments in the area of palladacycles and coordinatively unsaturated Pd catalysts featuring bulky phosphanes of high denticity like 107-109 ( Figure 11) These palladacycles are reviewed from a mechanistic and synthetic standpoint, and compared with more traditional catalysts obtained from conventional mono-and polydentate N and P-based ligands, as well as Pd catalysts without strong ligands, such as Pd colloids or heterogeneous catalysts and polymer supported catalysts.…”

Section: Reactions Involving Aryl Chlorides and Bromidesmentioning

confidence: 99%

Section: Reactions Involving Aryl Chlorides and Bromidesmentioning

confidence: 99%

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Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

181

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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Section: Reactions Involving Aryl Chlorides and Bromidesmentioning

confidence: 99%

Section: Reactions Involving Aryl Chlorides and Bromidesmentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

181

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“…The Heck reaction, the coupling of sp 2 -halides with alkenes promoted by palladium catalysts, is an important reaction for the synthesis of natural products and bioactive compounds as EtOH-DME (1 : 4) 90 well as for the industrial process chemistry. [110][111][112][113] Although many efforts to prepare solid-phase catalysts for the Heck reaction have been made, homogeneous catalytic systems have advantages on catalytic activity. [114][115][116][117][118][119][120][121][122] In fact, it was known that designing recyclable system for the Heck reaction was more challenging than that for the Suzuki-Miyaura reaction.…”

Section: Development Of a Novelmentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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IntroductionDevelopment of immobilized and insoluble metal catalysts is of great interest in recent organic chemistry. [1][2][3][4][5][6][7][8][9] The simple recovery of catalysts by filtration and their reuses resulted in enhancing the economical evaluation of the reaction. At the same time, there is a prospect that the environmental pollution caused by residual metals in the waste fluid will be decreased. Although a great deal of effort has been made to carry out such ideal reactions using immobilized metal catalysts, what seems to be lacking is the efficiency of the catalytic systems. It is obvious that the heterogeneous catalytic systems exhibit generally lower activity than the homogeneous ones. Besides, it is expected that the activity of the catalysts decreases gradually in the recycled systems because the metal species leaches away from their supports. Taking these into consideration, we decided to concentrate on developing insoluble metal catalysts which are highly active and stable. We designed that they were still effective in the use of ppm mol eq, and in the recycled use of many times in any reaction media. To achieve the challenging theme, we have focused on the amphiphilic insoluble catalysts based on a novel concept (Chart 1).Over the past few decades, a considerable numbers of study have been made on solid-phase catalysts which were immobilized with cross-linked polystyrene resins, silica gels or metals. These catalytic systems, however, generally resulted in lower catalytic activity compared with their soluble counterparts, and were often obliged to use hazardous chlorohydrocarbon solvents. [10][11][12][13][14][15] Besides, reuse of these catalysts was often difficult owing to the gradual decline of the catalytic activity. These problems made them less practical.In traditional triphase catalysts, as I have mentioned before, a catalytic species was anchored to a linker that was immobilized to a polymer resin or silica gel (Chart 1, above). In July 2005Chem. Pharm. Bull. 53(7) 723-739 (2005)

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“…We selected aryl iodide as a reactive group for labeling because it was known that the reactivity order of aryl halides in Mizoroki-Heck reactions is usually aryl iodide > aryl bromide > aryl chloride [16]. DIBI could be obtained by the relatively simple reaction as described in section 2.2.…”

Section: Fluorescence Characteristics Of Dibi and Dib-alprenololmentioning

confidence: 99%

Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction

Kishikawa

Ohkuma

Wada

et al. 2011

Journal of Chromatography A

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A novel fluorescent labeling method for alprenolol was developed based on Mizoroki-Heck coupling reaction. We designed and synthesized fluorescent aryl iodide, 4-(4,5-diphenyl-1H-imidazol-2-yl)iodobenzene (DIBI) as a labeling reagent.DIBI has a lophine skeleton carrying an iodide atom acting as fluorophore and reactive center, respectively. In order to evaluate the usefulness of DIBI, a highperformance liquid chromatography (HPLC) with fluorescence detection method was developed for the determination of alprenolol as a model compound of terminal double bond. The fluorescent labeling of alprenolol with DIBI was achieved in the presence of palladium acetate as a catalyst, and the labeled alprenolol was detected fluorometrically. In addition, it was found that the fluorescence of DIBI derivative increased and red shifted when compared that of DIBI. Furthermore, the proposed method could be applied to determine the alprenolol concentration in rat plasma after administration of alprenolol without interferences from biological components. The detection limit (S/N=3) for alprenolol in rat plasma was 0.74 ng/mL (30 fmol on column).

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Advances in the Heck chemistry of aryl bromides and chlorides

Cited by 592 publications

References 110 publications

Heck Reaction—State of the Art

Heck Reaction—State of the Art

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction

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