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4 edition of The preparation of C-aryl glucals via palladium mediated cross-coupling reactions found in the catalog.

The preparation of C-aryl glucals via palladium mediated cross-coupling reactions

Richard William Loo

The preparation of C-aryl glucals via palladium mediated cross-coupling reactions

by Richard William Loo

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Published by National Library of Canada = Bibliothèque nationale du Canada in Ottawa .
Written in English


Edition Notes

SeriesCanadian theses = Thèses canadiennes
The Physical Object
FormatMicroform
Pagination1 microfiche : negative.
ID Numbers
Open LibraryOL14909811M
ISBN 100315740132
OCLC/WorldCa30070925

  A simple and efficient palladium-catalyzed carbon–oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers. The development of new palladium catalysts for the cyanation of various aryl and heteroaryl chlorides is described. The combination of amine co‐catalysts with chelating phosphine ligands, for example, 1,4‐bis(diphenylphosphino)butane (dppb) or 1,5‐bis(diphenylphosphino)pentane (dpppe), allows an efficient cyanation of chloroarenes with simple potassium cyanide.

We undertook our investigation of the palladium(0)- catalyzed cross-coupling reaction by adding one-third of an equivalent of 1 to a boiling solution of iodobenzene and Pd- (PPh 3) 2 Cl 2 (2 mol %). Within 1 h, consumption of starting material was complete as evidenced by TLC and GC-MS analysis. Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophenecarboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or .

see article for more examples. Abstract. A range of biaryl compounds can be efficiently prepared in high yields by a palladium-catalyzed cross-coupling reaction between ortho-substituted triarylindium reagents and aryl triarylindium reagents are prepared by directed ortho-lithiation and transmetallation to indium from the corresponding benzene derivatives.   The recent developments in direct arylation reactions forming aryl–aryl bond have emerged as very attractive alternatives to traditional cross-coupling reactions.


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The preparation of C-aryl glucals via palladium mediated cross-coupling reactions by Richard William Loo Download PDF EPUB FB2

The C-aryl glucals 17–31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (11) and aryl bromides.

The major by-product in all of these reactions is the di the product of homocoupling of Cited by:   Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions. Organic Letters13 (17), DOI: /olm.

Scott E. Denmark, Christopher S. Regens, and, Tetsuya by: Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions. Organic Letters13 (17), DOI: /olm.

Guodong Liu, Jacqueline M. Wurst and Derek S. by: LiCl-Mediated Preparation of Functionalized Benzylic Indium(III) Halides and Highly Chemoselective Palladium-Catalyzed Cross-Coupling in a Protic Cosolvent. Angewandte Chemie International Edition48 (12), DOI: /anieCited by: Microwave-assisted palladium-catalyzed cross-coupling reactions between pyranoid glycals and aryl bromides.

Synthesis of 2′-deoxy C-aryl-β-glycopyranosides. Tetrahedron Letters50 (36), Cited by: The C-aryl glucals 17–31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (11) and aryl bromides.

@article{osti_, title = {Synthesis of C-glycosides via a palladium mediated coupling reaction of an aryl stannane and a glycal.

A study directed toward the synthesis of the gilvocarcins}, author = {Outten, R A}, abstractNote = {Tetrahydrodibenzocoumarin and -glycosides, similar in structure to the antibiotic gilvocarcins, were synthesized selectively at.

A novel and efficient methodology that allows for the construction of CP bonds via the palladium‐catalyzed oxygen‐based oxidative cross‐coupling of various arylhydrazines with H‐phosphonates leading to valuable arylphosphonates has been developed with the use of O2as the green oxidant; the method has broad substrate applicability and furnishes good to excellent yields.

A new method for the synthesis of protected benzamidines is described. The commercially available 1,3-bis(tert-butoxycarbonyl)methylthiopseudourea guanidylation reagent, after SEM-protection, functions as an amidine-forming cross-coupling partner under Liebeskind−Srogl conditions. In the presence of copper(I) thiophenecarboxylate (CuTC), the palladium-catalyzed cross-coupling of the.

Reductive elimination from complex II provides the aryl acetate () and regenerates the palladium(0) catalyst. /[~OOR Scheme 1 Pdn la-e Pd-Br 0 oG (OR I I CuBrF In conclusion, we have examined three sets of reaction conditions that effect the cross-coupling of the silylketene acetal derived from t-butyl acetate with a series of aryl.

Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross‐coupling of aryl chlorides and tosylates with appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4‐toluenesulfonyl).

In the past decade, palladium‐catalyzed C H activation/C C bond‐forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross‐coupling reactions using aryl and alkyl halides.

This Review begins with a brief introduction of four extensively investigated modes of catalysis. organoboronic acids is one of the most important palladium-catalyzed cross-coupling reactions of both academic and industrial interest.

In particular for the preparation of biaryl-containing molecules [13,14]. The reaction is the organic reaction of an aryl- or vinylboronic acid with an aryl or vinylhalide catalyzed by a palladium (0) complex.

ChemInform Abstract: Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions Between Pyranoid Glycals and Aryl Bromides. Synthesis of 2⠲-Deoxy C-Aryl-β-glycopyranosides Article. Promoted by cupric acetate and in the absence of additional ligand and base, the cross-coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields at room temperature under neutral and ambient conditions.

X.-m. Wu, Y. Wang, Synlett,25, Decarboxylative cross coupling reactions are chemical reactions in which a carboxylic acid is reacted with an organic halide to form a new carbon-carbon bond, concomitant with loss of CO 2. Aryl and alkyl halides participate. Metal catalyst, base, and oxidant are required.

The copper‐mediated C(aryl) N, C(aryl) O, and C(aryl) S bond formation is an important transformation and has been developed to include a wide range of substrates.

This Review highlights the recent developments in the copper‐mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and.

InZou et al. reported a new procedure for constructing arylalkynes through cross-coupling of terminal alkynes with arylboronic acids catalyzed by a palladium–silver system under mild conditions. 4 Very recently, Wu and co-workers described the cross-coupling reaction of arylboronic reagents with terminal alkynes catalyzed by.

Preparation of C-Aryl Glucals via the Palladium-Catalyzed Coupling of Metalated Aromatics with 1-Iodo-3,4,6-tri-O-(triisopropylsilyl)-D- glucal Article Aug Palladium-catalyzed cross-coupling reactions are state-of-the art methods for synthesis of many important compounds.

The development of the use of the phenol-derived sulfonated hydroxyl group in the coupling reactions is highly attractive as the hydroxyl group is commonly present in organic compounds and they are versatile alternatives to aryl halides in cross-coupling reactions.

Biaryl units constitute important building blocks in natural products and advanced materials, 2. The palladium-mediated cross-coupling reaction between aryl halides and arylboronic acids (the Suzuki reaction) has proven to be a versatile and highly useful method for the preparation of biaryl-containing molecules.

Here, we report a simple and powerful bioinspired strategy for the stereoselective synthesis of C-aryl glycosides via palladium-catalysed ortho-directed C(sp .Palladium- and copper-mediated N-arylations are important tools in organic synthesis. Due to the widespread importance of aryl-N bond formation, many synthetic methods have emerged over the years.

Besides the traditional Ullmann [1,2] and Gold-berg [] procedures, the palladium-catalysed reaction .