Palladium‐Catalyzed Intramolecular Decarboxylative Coupling of Arene Carboxylic Acids/Esters with Aryl Bromides

Abstract

Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad.

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

“…24,25,26,27,28,29,30,31 We were inspired by a report from Myers et al 32,33,34 detailing a palladium catalyzed decarboxylative Heck coupling under mild conditions. Based on those initial reports, our group reported 35 the mildest and most efficient method for aromatic decarboxylation utilizing catalytic amounts of a palladium complex.…”

A Novel Linking Strategy of Using 9,10‐Dihydroacridine to Construct Efficient Host Materials for Red Phosphorescent Organic Light‐Emitting Diodes

“…The structures and the synthesis routes of the three 4‐position 9,10‐dihydroacridine derivatives (MeAcPhCN, PhAcPhCN, and MeAcPyCN) are outlined in Scheme . The methyl 2‐[(2‐bromophenyl)amino]benzoate ( 1 ) precursor was prepared according to a method in the literature with 2‐aminobenzoate and 1‐bromo‐2‐iodobenzene as the starting materials . Treatment of 1 with a Grignard reagent (phenylmagnesium chloride) in THF was followed by the Friedel–Crafts alkylation reaction under acidic conditions, which gave cyclization product 2 .…”

“…The structures andt he synthesis routes of the three 4-position 9,10-dihydroacridine derivatives (MeAcPhCN, PhAcPhCN, and MeAcPyCN) are outlined in Scheme3.T he methyl 2-[(2-bromophenyl)amino]benzoate (1)p recursor was prepared according to am ethod in the literature with 2-aminobenzoate and 1bromo-2-iodobenzene as the starting materials. [25] Treatment of 1 with aG rignard reagent (phenylmagnesium chloride) in THF was followed by the Friedel-Crafts alkylation reaction under acidic conditions, which gave cyclization product 2. Then, the Pd-catalyzedS uzuki-Miyaura coupling reactionw ith the corresponding boric acid esters of [1,1'-biphenyl]-4-carbonitrile [26] and 5-phenylpicolinonitrile [27] yielded 3 and 4,r espectively.F inally,t he target MeAcPhCN and MeAcPyCN materials were obtained by am ethylation reaction, and PhAcPhCN was prepared by aC u-catalyzed Ullmann CÀNc oupling reaction.…”

Pd‐catalyzed bicyclization of 2‐alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans: a DFT study

“…The results suggested that the substrates with coordinating groups provided good selectivity for reactions of the alkyl‐substituted olefins. Shen et al . have investigated practical and efficient protocol for the palladium‐catalyzed intramolecular arylation of arene carboxylic acids with aryl halides through a decarboxylative cross‐coupling pathway under mild conditions.…”