Pd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C–N Bond Activation

Abstract

An efficient synthesis of tertiary amides from aryl boronic acids and inert tertiary amines through the oxidative carbonylation via C­(sp3)–N bond activation is presented. This protocol significantly restricts the homocoupling biarylketone product. It involves the use of a homogeneous PdCl2/CuI catalyst and a heterogeneous Pd/C based catalyst, which promotes C­(sp3)–N bond activation of tertiary amines with aryl boronic acids. This process represents a ligand-free, base-free, and recyclable catalyst along with an ideal oxidant like molecular oxygen.

Synthesis of Diarylselenides through Rh-Catalyzed Direct Diarylation of Elemental Selenium with Benzamides

“…All manipulations were performed under N 2 using standard Schlenk techniques unless otherwise noted. Amide compounds were prepared by standard condensation of the corresponding acid chlorides and amines similarly to the literature: all 1 and 3 are known in the literature . [Cp E RhCl 2 ] 2 was prepared according to the literature procedure .…”

Magnetically separable Ni/Fe3O4: An efficient catalyst for phenoxy carbonylation of aryl iodides using bifunctional o‐chlorophenyl formate as a CO source

“…[23,24] Based on our long-term interests in transition metalcatalyzed carbonylative reactions, we encourage continued enthusiasm for transition metal-catalyzed carbonylation reactions. [25][26][27][28] Herein, we have developed a magnetically separable heterogeneous catalytic system Ni/Fe 3 O 4 for phenoxy carbonylation of aryl iodide using o-chlorophenyl formate. This CO surrogate helps to eliminate the direct use of hazardous carbon monoxide gas and the use of o-chlorophenol generated in the reaction to act as a coupling partner in the presence of a nickel catalyst (Scheme 1c).…”

Tunable Pd/C-catalyzed oxidative alkoxycarbonylation/aminocarbonylation of aryl hydrazines with alcohols/inert tertiary amines through C–N bond activation

“…16 In this regard, our group also reported oxidative aminocarbonylation of aryl halide and aryl boronic acid with tertiary amide via sp 3 C–N bond activation and double carbonylation of tertiary amines with alcohols. 17 The one-pot oxidative carbonylation reaction between aryl hydrazine and inert tertiary amines via C–N bond activation is challenging. As far as we know, the oxidative aminocarbonylation of aryl hydrazine with an unreactive tertiary amine through C–N bond activation to convert the corresponding tertiary amides is not yet reported.…”