102631-08-3

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 121-90-4 m-nitrobenzoic acid chloride 
• 85107-44-4 2-(3-nitro-phenyl)-[1,3,2]dioxaborinane 
• 54132-75-1 3,5-dimethylphenyl isocyanate 
• 203321-89-5 (3,5-dimethylphenyl)carbamic acid 1,1-dimethylethyl ester 
• 220210-17-3 tris(3-nitrophenyl)-1,3,5,2,4,6-trioxatriborinane 

Downstream Products

• 102630-90-0 3-Amino-N-(3,5-dimethyl-phenyl)-benzamide 

Relevant academic research and scientific papers

PROCESS FOR DIRECT AMIDATION OF AMINES VIA RH(I)-CATALYZED ADDITION OF BOROXINES

This invention relates to a process for making an amide by directly reacting a ferf-butyloxycarbonyl or carboxybenzyl N substituted amine with a boroxine derivative in the presence of a rhodium(l) catalyst, in the presence of a solvent an optionally in the presence of a base. The process provides means to react protected amines to amides using th boroganic reagent without the deprotection of an amine such that it can be directly converted from protected form in on step, and results in good yields in amide formation even for sterically hindered amines. Potassium fluoride is the preferre base in the reaction run in dioxane. Typical rhodium catalysts that can be used include rhodium(l) complex monomer and dimers such as chloro(1,5-cyclooctadiene) rhodium(l) dimer ("[CI(cod)Rh]2") or bis(1,5-cyclooctadiene)rhodium(l trifluoromethanesulfonate ("(cod)2Rh(OTf)").

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

Copper(i)-catalyzed amidation reaction of organoboronic esters and isocyanates

A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using a ligand-free copper(i) catalyst. The reaction system demonstrated a broad substrate scope and provided convenient access to a wide variety of secondary amides.