Biaryl Synthesis via Decarboxylative Pd-Catalyzed Reactions of Arenecarboxylic Acids and Diaryliodonium Triflates

Becht, Jean‐Michel; Drian, Claude Le

doi:10.1021/ol8011293

Cited by 140 publications

(31 citation statements)

References 46 publications

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“…Using this method, a vast range of highly substituted, nonsymmetrical biaryls could be readily prepared (Scheme 25). [121] Scheme 21. a) Catalytic cycle for copper-catalyzed arylation and b) C3À C2 bond migration. …”

Section: Angewandte Chemiementioning

confidence: 99%

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009

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The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.

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Section: Angewandte Chemiementioning

confidence: 99%

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009

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“…[18,21] Becht et al showed that the use of silver in overstoichiometric amounts is advantageous especially for methoxy-substituted arenecarboxylates. [22] Steglich, [23] Forgione and Bilodeau [24] discovered a different catalytic pathway for palladium-catalyzed decarboxylative crosscouplings, which is applicable specifically to five-ring heteroarenes bearing a carboxylate group in the 2-position. In their protocol, the carbopalladation presumably precedes the decarboxylation, so that the position of the carboxylate group is not the primary factor that defines the position of carbon À carbon bond formation.…”

Section: Introductionmentioning

confidence: 99%

Biaryl and Aryl Ketone Synthesis via Pd‐Catalyzed Decarboxylative Coupling of Carboxylate Salts with Aryl Triflates

Gooßen

Linder

Rodríguez

et al. 2009

Chemistry A European J

128

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A bimetallic catalyst system has been developed that for the first time allows the decarboxylative cross-coupling of aryl and acyl carboxylates with aryl triflates. In contrast to aryl halides, these electrophiles give rise to non-coordinating anions as byproducts, which do not interfere with the decarboxylation step that leads to the generation of the carbon nucleophilic cross-coupling partner. As a result, the scope of carboxylate substrates usable in this transformation was extended from ortho-substituted or otherwise activated derivatives to a broad range of ortho-, meta-, and para-substituted aromatic carboxylates. Two alternative protocols have been optimized, one involving heating the substrates in the presence of Cu(I)/1,10-phenanthroline (10-15 mol %) and PdI(2)/phosphine (2-3 mol %) in NMP for 1-24 h, the other involving Cu(I)/1,10-phenanthroline (6-15 mol %) and PdBr(2)/Tol-BINAP (2 mol %) in NMP using microwave heating for 5-10 min. While most products are accessible using standard heating, the use of microwave irradiation was found to be beneficial especially for the conversion of non-activated carboxylates with functionalized aryl triflates. The synthetic utility of the transformation is demonstrated with 48 examples showing the scope and limitations of both protocols. In mechanistic studies, the special role of microwave irradiation is elucidated, and further perspectives of decarboxylative cross-couplings are discussed.

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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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Biaryl Synthesis via Decarboxylative Pd-Catalyzed Reactions of Arenecarboxylic Acids and Diaryliodonium Triflates

Cited by 140 publications

References 46 publications

Diaryliodonium Salts: A Journey from Obscurity to Fame

Diaryliodonium Salts: A Journey from Obscurity to Fame

Biaryl and Aryl Ketone Synthesis via Pd‐Catalyzed Decarboxylative Coupling of Carboxylate Salts with Aryl Triflates

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

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