Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature

Li, Mingzong; Ge, Haibo

doi:10.1021/ol200459v

Cited by 120 publications

(35 citation statements)

References 50 publications

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“…The identity of obtained ketones 3a, [24] 3b, [25] 3c, [24] 3d, [24] 3e, [24] 3f, [24] 3g, [24] 3h, [24] 3j, [26] 3k, [27] 3l [24] and 3m [28] was assessed by comparison of their 1 Ha nd 13 CNMR spectroscopic data with those reported in the literature. In ag lass tube, the appropriate nitrile (0.5 mmol) was added to the corresponding alternative solvent (0.5 g) under air,f ollowed by the addition of PhLi (1 mmol) at room temperature, and the reaction mixture was stirred for 2-3 s. The reaction was then stopped by addition of as aturated solution of the Rochelle salt (sodium potassium tartrate tetrahydrate).…”

Section: Methodsmentioning

confidence: 99%

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Rodríguez-Álvarez

García‐Álvarez

Uzelac

et al. 2018

Chemistry A European J

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Edging closer towards developing air and moisture compatible polar organometallic chemistry, the chemoselective and ultrafast addition of a range of aryllithium reagents to nitriles has been accomplished by using glycerol as a solvent, at ambient temperature in the presence of air, establishing a novel sustainable access to aromatic ketones. Addition reactions occur heterogeneously ("on glycerol conditions"), where the lack of solubility of the nitriles in glycerol and the ability of the latter to form strong intermolecular hydrogen bonds seem key to favouring nucleophilic addition over competitive hydrolysis. Remarkably, PhLi exhibits a greater resistance to hydrolysis working "on glycerol" conditions than "on water". Introducing glycerol as a new solvent in organolithium chemistry unlocks a myriad of opportunities for developing more sustainable, air and moisture tolerant main-group-metal-mediated organic synthesis.

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Section: Methodsmentioning

confidence: 99%

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Rodríguez-Álvarez

García‐Álvarez

Uzelac

et al. 2018

Chemistry A European J

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“…(2‐Naphthalenyl)(phenyl)methanone (4p): White solid, 223 mg (96 %); m.p. 82.4–83.4 °C; R f = 0.63 (EtOAc/hexane = 1:5).…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylative Coupling Reactions of N,N‐Bis(methanesulfonyl)amides through C–N Bond Cleavage

et al. 2018

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Palladium‐catalyzed carbonylative coupling reactions of various N,N‐bis(methanesulfonyl)amides with arylboronic acids through C–N bond cleavage were carried out. The reactions proceeded under mild conditions in a short period of time without any additives to afford a wide range of unsymmetrical aryl ketones in excellent yields. This is the first example of a carbonylative coupling reaction using N,N‐bis(methanesulfonyl)amide as a coupling substrate.

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“…Ge et al reported decarboxylative cross-coupling of trifluoro(organo)borates with 2-ketone acids [66], oxalate monoesters [67], and 2-amino-2-oxoacetates [67] (Scheme 53). This reaction affords aryl ketones, esters, and amides as the products.…”

Section: Cross-coupling Between Ccooh and Cm Bondsmentioning

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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Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature

Abstract: A novel Pd-catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with α-oxocarboxylic acids is performed at room temperature. This reaction provides an efficient access to aryl ketones under mild conditions.

Cited by 120 publications

References 50 publications

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Palladium‐Catalyzed Carbonylative Coupling Reactions of N,N‐Bis(methanesulfonyl)amides through C–N Bond Cleavage

Transition metal-catalyzed decarboxylative cross-coupling reactions

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