Copper(II)-Catalyzed Esterification of Arenecarboxylic Acids with Aryl- and Vinyl-Substituted Trimethoxysilanes

Luo, Fang; Pan, Changduo; Qian, Peng‐Cheng; Cheng, Jiang

doi:10.1055/s-0029-1218759

Cited by 9 publications

(1 citation statement)

References 5 publications

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“…The in situ version was also established by Albiniak et al [105]. Cu-mediated coupling reactions using aryl trialkoxysilanes [106] or arylboronic acids [107] were developed by Cheng et al (Figure 2 (b)). Diaryliodonium salts were found to be good electrophiles for the esterification (Figure 2 (c)) [108].…”

Section: The Use Of Electrophile Equivalentsmentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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In this chapter, recent advances in the synthesis of carboxylic acid esters are summarized based on the utilization of carboxylic acids as electrophiles or nucleophiles in reactions. Condensation reagents or catalysts connect the carboxylic acids with the alcohols to afford the corresponding esters, together with the formation of 1 equiv. of H 2 O, in which the carboxylic acids can be regarded as the electrophile. In contrast, the carboxylate ion intermediates derived from the carboxylic acids react with alkyl halides, carbocations, or their equivalents to produce the esters, in which the carboxylate ions from the carboxylic acids can be regarded as the nucleophile. This chapter mainly introduces the recent progress in this field of the formation of esters, based on the classification of the role of carboxylic acids in reactions.

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Section: The Use Of Electrophile Equivalentsmentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid

2015

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The oxidative coupling of alkylboronic acids with oxygen nucleophiles offers a strategy for replacing toxic, electrophilic alkylating reagents. Although the Chan-Lam reaction has been widely applied in the arylation of heteroatom nucleophiles, O-alkylation with boronic acids is rare. We report a Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid that proceeds in air with no additional oxidant. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.

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Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

Zhang

Hou

et al. 2018

J. Org. Chem.

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A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.

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Copper(II)-Catalyzed Esterification of Arenecarboxylic Acids with Aryl- and Vinyl-Substituted Trimethoxysilanes

Cited by 9 publications

References 5 publications

Recent Advances in the Synthesis of Carboxylic Acid Esters

Recent Advances in the Synthesis of Carboxylic Acid Esters

Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid

Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

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