Palladium-Catalyzed C−H Bond Functionalization with Arylsulfonyl Chlorides

Zhao, Xiaodan; Dimitrijević, Elena; Dong, Vy M.

doi:10.1021/ja900200g

Cited by 445 publications

(183 citation statements)

References 32 publications

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“…Their uses as coupling partners in C-H bond functionalization are more recent. Based on Dong's pioneering work on Pd-catalyzed C-H bond sulfonylation of 2-phenylpyridines using benzenesulfonyl chlorides as coupling partners, in which they observed a desulfitative coupling in one case [64], Cheng and co-workers reported the use of benzenesulfonyl chlorides as aryl sources for the direct arylation of benzoxazoles (Scheme 10) [65]. The reaction displays a broad scope including substrates bearing C-Br bonds.…”

Section: Benzoic Acidsmentioning

confidence: 99%

New Arylating Agents in Pd-Catalyzed C–H Bond Functionalization of 5-Membered Ring Heteroarenes

Soulé

Doucet

2015

C-H Bond Activation and Catalytic Functionalization I

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In recent years, the palladium-catalyzed direct arylation of heteroaromatics via C-H bond activation has become a popular method for generating carbon-carbon bonds. In most cases, aryl halides were employed as the coupling partners. However, since a few years, several new coupling partners have emerged as useful alternatives for such couplings. This chapter focuses on the recent advances on the discovery of new arylating agents in the palladium-catalyzed arylation of 5-membered ring heteroaromatics.

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Section: Benzoic Acidsmentioning

confidence: 99%

New Arylating Agents in Pd-Catalyzed C–H Bond Functionalization of 5-Membered Ring Heteroarenes

Soulé

Doucet

2015

C-H Bond Activation and Catalytic Functionalization I

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“…65 In most cases these transformations involve intramolecular reactions. The first example of 16 an intramolecular catalytic process was developed by Inamoto and Doi (Figure 19a As far as we know, the only example of intermolecular C-S bond formation was recently reported by Dong et al 68 The approach developed allows for the functionalization of 2-phenylpyridines 55 (Figure 19d …”

Section: -Carbon-sulfur and Carbon-phosphorus Bond Formationmentioning

confidence: 99%

“…31 In the second one, an innovative halogenation approach based on the combination of Pd and electrochemical oxidation permits to functionalize arylpyridines 45 to give excellent yields of 46, and eliminates the need to remove the remaining oxidant or its byproducts. 32 In this method HX (X=Cl, Br) play a dual role, working as both supporting electrolyte and source of the halogen.…”

mentioning

confidence: 99%

Orthometallation as a Strategy in Pd-mediated Organic Synthesis

Camaño¹,

Cuesta²,

Nieto³

et al. 2011

COC

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Abstract:The orthopalladated complexes are among the most representative Pd(II) compounds. They display a wide prospect of applications, but they are mainly known by their use as intermediates in metal-mediated organic synthesis. In this review we describe how palladacycles are used to build up new molecules through regioselective formation of C-halogen, C-O, C-N, C-P, C-S and C-C bonds, either under catalytic or stoichiometric conditions. This methodology is based on the selective incorporation of the Pd into the organic skeleton to be modified and subsequent reactivity of the Pd-C bond toward different substrates. In many cases this strategy is alternative or even competitive, improving standard organic methods. The most recent achievements of the last five years will be covered here, presenting only the most impressive results.

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“…On the other hand, Wang and al. extended this coupling to 4-bromobenzenesulfinic acid in acidic conditions and microwave heating (Figure 1c During the last decade, benzenesulfonyl chloride coupling partners have been used for the direct arylation of benzoquinoline, 20 azoles, 21 thiophenes, 22 (benzo)furans 23 and pyrroles. 24 Recently, we reported on Pd-catalyzed chemoselective direct desulfitative arylation of heteroarenes using (poly)halobenzenesulfonyl chlorides, 25 which allowed sequential arylations.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides

et al. 2016

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. Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-: N -protected indoles using (hetero)arenesulfonyl chlorides. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2016, 14 (21) The direct arylation of N-protected 3-haloindole derivatives with benzenesulfonyl chlorides as coupling partners using 5 mol% of bis(acetonitrile)dichloropalladium(II) catalyst and lithium carbonate as base in 1,4-dioxane was investigated. We demonstrated that both iodo and chloro substituents at indolyl C3 position act as temporary blocking groups to allow the formation of 2-arylindoles through a direct desulfitative arylation, followed by in-situ dehalogenation. While, from 3-bromoindole derivatives, 2-aryl-3-bromoindoles were obtained without debromination, and could be converted into 2,3-diarylindoles through a second palladium coupling. which are both of interest as potential intermediates in the synthesis of bioactive molecules.

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Palladium-Catalyzed C−H Bond Functionalization with Arylsulfonyl Chlorides

Cited by 445 publications

References 32 publications

New Arylating Agents in Pd-Catalyzed C–H Bond Functionalization of 5-Membered Ring Heteroarenes

New Arylating Agents in Pd-Catalyzed C–H Bond Functionalization of 5-Membered Ring Heteroarenes

Orthometallation as a Strategy in Pd-mediated Organic Synthesis

Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides

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