A facile method for Rh-catalyzed decarbonylative <i>ortho</i>-C–H alkylation of (hetero)arenes with alkyl carboxylic acids

Tian, Yiqiang; Liu, Xiaojie; He, Bangyue; Ren, Yuxi; Su, Weiping

doi:10.1039/d1ra03992j

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2023

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Cited by 2 publications

References 68 publications

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CH Functionalization Using Carboxylic Acids and Carboxylic Acid Derivatives as Electrophiles under Redox‐Neutral Conditions

Gao¹,

Meng²,

Hammadi³

et al. 2022

Handbook of CH-Functionalization

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The article provides a summary of the recent developments in using carboxylic acids and derivatives as aryl, alkenyl, and alkyl electrophiles for CH functionalization. This manifold exploits ubiquitous carboxylic acids as electrophiles after oxidative addition and decarbonylation in the absence of external oxidants under Rh, Pd, Ni, and Ir catalysis. Mechanistically, acyl RC(O)X bond oxidative addition to low valent metals is followed by decarbonylation, resulting in a net generation of R[M] electrophiles for a broad range of CH functionalization processes. The article covers aroyl chlorides, aroyl fluorides, anhydrides, carboxylic acids, esters and amides, and other related acyl derivatives.

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CH Functionalization Using Carboxylic Acids and Carboxylic Acid Derivatives as Electrophiles under Redox‐Neutral Conditions

Gao¹,

Meng²,

Hammadi³

et al. 2022

Handbook of CH-Functionalization

View full text Add to dashboard Cite

show abstract

Rh‐Catalyzed Direct Decarbonylative Borylation of Carboxylic Acids

Yin

Liao

et al. 2023

Chemistry A European J

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Carboxylic acids are abundant, low cost and environmentally friendly, direct convert carboxylic acids into valued‐added compounds are in high demand. Herein, we report a Rh(I) catalyzed direct decarbonylative borylation of aryl and alkyl carboxylic acid using TFFH as activator. This protocol features excellent functional‐group tolerance and a broad substrate scope including natural product and drugs. A gram‐scale decarbonylative borylation reaction of Probenecid is also presented. In addition, the utility of this strategy is highlighted by a one‐pot decarbonylative borylation/ derivatization sequence.

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A facile method for Rh-catalyzed decarbonylative ortho-C–H alkylation of (hetero)arenes with alkyl carboxylic acids

Abstract: A facile and effective method for Rh-catalyzed direct ortho-alkylation of C–H bonds in (hetero)arenes with commercially available carboxylic acids has been developed.

Cited by 2 publications

References 68 publications

CH Functionalization Using Carboxylic Acids and Carboxylic Acid Derivatives as Electrophiles under Redox‐Neutral Conditions

CH Functionalization Using Carboxylic Acids and Carboxylic Acid Derivatives as Electrophiles under Redox‐Neutral Conditions

Rh‐Catalyzed Direct Decarbonylative Borylation of Carboxylic Acids

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