Low‐Temperature Ag/Pd‐Catalyzed Decarboxylative Cross‐Coupling of Aryl Triflates with Aromatic Carboxylate Salts

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

doi:10.1002/chem.200903319

Cited by 119 publications

(45 citation statements)

References 49 publications

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“…[77] Subsequently, the catalysis underwent continuous improvement, such as microwave heating, [78] the use of aryl tosylates instead of aryl triflates, [79] or the introduction of silver decarboxylation at only 120 8C, which is more than 50 8C lower than the best copper catalysts known. [80] The percentages of Pd and Cu or Ag used were also reduced to the range 2 % Pd and 5 % Cu or Ag, much lower figures than in the initial studies.…”

Section: A C H T U N G T R E N N U N G (Pph 3 ) 2 ]/A C H T U N G T Rmentioning

confidence: 93%

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Pérez‐Temprano

Casares

Espinet

2012

Chemistry A European J

217

131

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Bimetallic catalysis refers to homogeneous processes in which either two transition metals (TM), or one TM and one Group 11 (G11) element (occasionally Hg also), cooperate in a synthetic process (often a C-C coupling) and their actions are connected by a transmetalation step. This is an emerging research area that differs from the isolated or tandem applications of the now classic processes (Stille, Negishi, Suzuki, Hiyama, Heck). Most of the reactions used so far combine Pd with a second metal, often Cu or Au, but syntheses involving very different TM couples (e.g., Cr/Ni in the catalyzed vinylation of aldehydes) have also been developed. Further development of the topic will soon demand a good knowledge of the mechanisms involved in bimetallic catalysis, but this knowledge is very limited for catalytic processes. However, there is much information available, dispersed in the literature, coming from basic research on exchange reactions occurring out of any catalytic cycle, in polynuclear complexes. These are essentially the same processes expected to operate in the heart of the catalytic process. This Review gathers together these two usually isolated topics in order to stimulate synergy between the bimetallic research coming from more basic organometallic studies and the more synthetic organic approaches to this chemistry.

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Section: A C H T U N G T R E N N U N G (Pph 3 ) 2 ]/A C H T U N G T Rmentioning

confidence: 93%

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Pérez‐Temprano

Casares

Espinet

2012

Chemistry A European J

217

131

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“…[24] As long as the substrates do not contain such groups, competing decarboxylative ipso substitution would thus effectively be suppressed. The carboxylate ion is likely to be directly transferred to the silver co-catalyst (f, g), and the catalytic cycle is closed by reoxidation of the copper center (a).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Aryl Ethers from Benzoates through Carboxylate‐Directed CH‐Activating Alkoxylation with Concomitant Protodecarboxylation

2013

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Scheme 3. Scope of the directed etherification of aromatic carboxylates. Reaction conditions: 1.00 mmol 1 a-t, 1.20 mmol 2 a-i, 0.25 mmol Cu(OAc) 2 , 1.00 mmol Ag 2 CO 3 , 1 atm. O 2 , 5 mL DMF, 140 8C, 36 h. [a] With 5 mmol B(OR) 3 . [b] With 10 % methylester. [c] With 12 % methylester. [d] With 19 % quinoline.Scheme 4. Alkoxylation with a trialkoxyborate that was generated in situ.Scheme 5. Evidence against the formation of (acetyl)phenols as intermediates.

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“…By doing so they successfully developed the first examples of the decarboxylative cross-coupling reactions catalytic in both Pd and Ag. Because for some substrates, silver complexes possess a higher decarboxylating acitivity than copper complexes, the Pd/Ag-catalyzed decarboxylative cross-coupling reactions can proceed under milder conditions as compared to the Pd/Cu-catalyzed ones [26].…”

Section: Biaryl Formationmentioning

confidence: 99%

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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Low‐Temperature Ag/Pd‐Catalyzed Decarboxylative Cross‐Coupling of Aryl Triflates with Aromatic Carboxylate Salts

Cited by 119 publications

References 49 publications

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Synthesis of Aryl Ethers from Benzoates through Carboxylate‐Directed CH‐Activating Alkoxylation with Concomitant Protodecarboxylation

Transition metal-catalyzed decarboxylative cross-coupling reactions

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