Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Gooßen, Lukas J.; Rodríguez, Nuria; Lange, Paul P.; Linder, Christophe

doi:10.1002/anie.200905953

Cited by 222 publications

(66 citation statements)

References 51 publications

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“…As a result, they were able to extend the above cross-coupling to aryl chlorides [18], triflates [19], and even tosylates (Scheme 10(b)) [20]. It was found that the chloride or bromide anion generated in the reaction can hamper the Cu-catalyzed decarboxylation process [21].…”

Section: Biaryl Formationmentioning

confidence: 98%

Transition metal-catalyzed decarboxylative cross-coupling reactions

2011

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Transition metal-catalyzed decarboxylative cross-coupling reactions have recently emerged as a new and important category of organic transformations that find versatile applications in the construction of carbon-carbon and carbon-heteroatom bonds. The use of relatively cheap and stable carboxylic acids to replace organometallic reagents enables the decarboxylative cross-coupling reactions to proceed with good selectivities and functional group tolerance. In the present review we summarize the various types of decarboxylative cross-coupling reactions catalyzed by different transition metal complexes. The scope and applications of these reactions are described. The challenges and opportunities in the field are discussed.

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Section: Biaryl Formationmentioning

confidence: 98%

Transition metal-catalyzed decarboxylative cross-coupling reactions

2011

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“…在"第二代催化剂"的基础上, Goossen 课题组 [47,48] 分别实现了 Pd/Cu 催化邻/间/对位取代的羧酸脱羧与 ArOTf [47] 或 ArOTs [48] [56] , 使用 DPEphos 配体可以获得满意的反应产率. 此外, 三价芳基碘盐具有稳定、易制备等优势 [57] .…”

Section: 脱羧 Heck 偶联反应unclassified

Recent Progress in Pd-Catalyzed Decarboxylative Coupling Reactions of (Hetero)aromatic Carboxylic Acids

付拯江¹,

李兆杰²,

熊起恒³

et al. 2015

Chin. J. Org. Chem.

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Since carboxylic acids have distinguishing features of non-toxicity, low cost, ready availability and easy storage, Pd-catalyzed decarboxylative coupling reactions of (hetero)aromatic carboxylic acids have been obtained rapid development since this century, and have exhibited a tendency toward replacement of traditional coupling reactions. The coupling reactions of Pd-catalyzed decarboxylation of aromatic carboxylic acids with various substrates of olefins, aryl halides, arenes, aryltrifluoroborates and etc. are reviewed, and the relevant reaction mechanisms are discussed.

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“…phenanthroline (Scheme 3.19) [35]. The reaction could be performed either using conventional heating (170 ∘ C, 4 h) or microwave heating (180 ∘ C, 2 min).…”

Section: Pd/cu-based Systemsmentioning

confidence: 99%

“…Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts, as described by Goossen and coworkers [35]. …”

Section: Scheme 319mentioning

confidence: 99%

Decarboxylative Coupling Techniques

2014

Catalytic Arylation Methods

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Science as an intellectual exercise enriches our culture, and is in itself ennobling … Though to the layman, the world revealed by the chemist may seem more commonplace, it is not so to him. Each new insight into how the atoms in their interactions express themselves in structure and transformations, not only of inanimate matter, but particularly also of living matter, provides a thrill.(Henry Taube) 3.1

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Decarboxylative Cross‐Coupling of Aryl Tosylates with Aromatic Carboxylate Salts

Cited by 222 publications

References 51 publications

Transition metal-catalyzed decarboxylative cross-coupling reactions

Transition metal-catalyzed decarboxylative cross-coupling reactions

Recent Progress in Pd-Catalyzed Decarboxylative Coupling Reactions of (Hetero)aromatic Carboxylic Acids

Decarboxylative Coupling Techniques

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