Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids

Abstract

A novel Pd-catalyzed decarboxylative ortho-acylation of acetanilides with alpha-oxocarboxylic acids is realized at room temperature. This reaction provides efficient access to o-acyl acetanilides under mild conditions.

A Highly Efficient Palladium‐Catalyzed Decarboxylative ortho‐Acylation of Azobenzenes with α‐Oxocarboxylic Acids: Direct Access to Acylated Azo Compounds

“…The palladium source was found to be crucial for this transformation and several commercially available Pd II salts were tested in the acylation of 1 a with 2 a at room temperature with K 2 S 2 O 8 as the oxidant and DCE as solvent. It should be noted that Pd(OAc) 2 exhibited high activity in the decarboxylative reaction, and was found to be more active than [Pd(TFA) 2 ] (TFA = trifluoroacetic acid) (Table 1, entry 7 vs entry 3) 4a. Several other Pd sources were screened, including PdCl 2 , [Pd(CH 3 CN) 2 Cl 2 ], and [Pd(PPh 3 ) 2 Cl 2 ], but did not enhance the yield of product 3 a (Table 1, entries 8–10).…”

Palladium‐Catalyzed Divergent Reactions of α‐Diazocarbonyl Compounds with Allylic Esters: Construction of Quaternary Carbon Centers

“…However, decarboxylation did not occur when using allyl 2-oxo-2-phenylacetate 4 l [Eq (1)]. [21] Finally, the molecular structure Table 2: Screening conditions for the palladium-catalyzed reaction of 4 a with 2 a.…”

Retracted: Palladium‐Catalyzed Decarboxylative Selective Acylation of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives with α‐Oxo Carboxylic acids via Preferential Cyclic Imine‐N‐Directed Aryl C−H Activation

“…[1] Since the pioneering work of Myers [2] and Goossen [3] this reaction has been usedf or C À Hf unctionalization of various systems.R ecently,d ecarboxylativea cylation using aoxo carboxylic acids hasb een successfully applied for ortho-acylation of acetanilides, [4] O-phenyl carbamates, [5] indoles, [6] azoxybenzenes, [7] and O-methyl ketoximes [8] among others. [1] Since the pioneering work of Myers [2] and Goossen [3] this reaction has been usedf or C À Hf unctionalization of various systems.R ecently,d ecarboxylativea cylation using aoxo carboxylic acids hasb een successfully applied for ortho-acylation of acetanilides, [4] O-phenyl carbamates, [5] indoles, [6] azoxybenzenes, [7] and O-methyl ketoximes [8] among others.…”