Palladium-catalyzed Reaction of Stannyl Sulfide with Aryl Bromide. Preparation of Aryl Sulfide

Kosugi, Masanori; Ogata, Toshimi; Terada, Masahiro; Sano, Hiroshi; Migita, Toshihiko

doi:10.1246/bcsj.58.3657

Cited by 189 publications

(60 citation statements)

References 5 publications

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“…The preparation of thioethers has been under consideration and widely studied in recent years using palladium [23], nickel [24], cobalt [25], copper [26] and iron salts [27] as catalysts. Migita et al [28] first reported the coupling of aryl halides with thiols using Pd(PPh 3 ) 4 as a catalyst. Recent methodologies include general protocols by Zheng et al using aryl triflates [29], coupling using DPEPhos as ligand [30]; thioetherification using CyPF-t-Bu as ligand [23].…”

Section: Introductionmentioning

confidence: 99%

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

2014

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This paper reports a series of novel metal acetylacetonates covalently anchored onto amine functionalized silica/starch composite, prepared by the Schiff condensation of metal acetylacetonates [Co(acac) 2 , Cu(acac) 2 , Pd(acac) 2 , Ru(acac) 3 , Mn(acac) 3 , Co(acac) 3 ] with organically modified 3-aminopropyl silica/starch composite. Different metal acetylacetonates have been chosen with a view to select the most active heterogeneous catalyst. Among various catalysts, covalently anchored Cu(acac) 2 onto amine functionalized silica/starch composite [ASS-Cu(acac) 2 ] was found to be the most active and recyclable catalyst for the one-pot thioetherification and one-pot three component synthesis of 2H-indazoles via consecutive C-N and N-N bond formations. All the catalysts were characterized by FTIR, TGA and AAS analysis and the most active catalyst, [ASS-Cu(acac) 2 ] was further characterized by SEM and TEM. The catalyst could be recovered by simple filtration and reused with almost consistent activity for four consecutive runs.

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Section: Introductionmentioning

confidence: 99%

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

2014

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“…The initial results concerning aryl halide amination and related results in chemistry forming aryl sulfides [93][94][95][96] and phosphines [97] strongly suggested that a mild, convenient route to arylamines from aryl halides could be developed. However, the source of the amido group had to be less toxic, more thermally stable, and less air-sensitive than a tin amide.…”

Section: 22mentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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“…5 Many other Pd based catalytic systems have also been developed, which are based on bidentate phosphines or diverse organophosphane derivatives. [6][7][8][9] But these systems have limitations since they require the preparation and use of PR 3 ligands which are not eco-friendly.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in copper-catalyzed C-S cross-coupling reactions

Asha¹,

Thomas²,

Thankachan³

et al. 2014

Arkivoc

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Copper-catalyzed cross-coupling reactions offer a powerful tool for the formation of carbonheteroatom bonds. Copper catalysis has an indisputable advantage over the other catalytic systems due to its low cost and the use of readily accessible and stable ligands. Among the various copper-catalyzed coupling reactions, C-S bond forming reactions have gained much attention due to its applications in the synthesis of molecules having biological and pharmaceutical impact. This review illustrates the current strategies and applications of Cucatalyzed C-S cross coupling reactions.

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Palladium-catalyzed Reaction of Stannyl Sulfide with Aryl Bromide. Preparation of Aryl Sulfide

Abstract: Tributylstannyl alkyl or aryl sulfide and bis(tributylstannyl) sulfide were found to be useful to prepare aryl sulfides in good yields under the usual conditions of the palladium-catalyzed reaction with aryl bromides.

Cited by 189 publications

References 5 publications

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Recent advances in copper-catalyzed C-S cross-coupling reactions

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