Palladium-Catalyzed Methylation and Arylation of sp² and sp³ C−H Bonds in Simple Carboxylic Acids

Abstract

The use of preformed sodium carboxylates as substrates led to the first observation of facile Pd-insertions into sp3 β-C−H bonds in simple aliphatic acids. Consequently, Pd-catalyzed methylation and arylation of o-C−H bonds in benzoic acids and β-C−H bonds in aliphatic acids using either a phenylboronate, methylboronic acid, or ArI have been achieved via a C−H activation/C−C coupling sequence.

Easily Modified Directing Groups for the Palladium-Catalyzed C—H Functionalization

“…随后该小组探索了一系列 Pd 催化 下的含氧诱导基作用的 C-H 活化反应 [11] , 在此领域开 了先河并作出了贡献. Yu 等 [13] 报道了羧基诱导的 α 位 sp 2 -C-H 键的甲基 化和 β 位 sp 3 -C-H 键的芳基化反应(Scheme 5 然而当使用 Cu(OTf) 2 作氧化剂, 在酸性溶剂 TFE 下, 富电子的苯乙酰胺偏向于得到二聚产物, 因此,…”

Wenn C‐H‐Bindungen sprechen könnten – selektive Oxidationen von C‐H‐Bindungen

“…[66] Ein hervorragendes Beispiel für die Eignung von Carbonsäuren als dirigierenden Gruppen für aliphatische C-H-Bindungen wird durch das Carbonsäuresub-strat 54 verdeutlicht.…”

“Greening Up” Cross-Coupling Chemistry

“…These stable organometallics have emerged as practical substrates for other arylation reactions as well. Although several examples have appeared using aryl boronic acids in ortho-directed C-H activation reactions with anilide derivatives, like most C-H activation protocols, these transformations generally require harsh conditions [35][36][37][38].…”