Efficient palladium-catalyzed amination of aryl chlorides using di(dicyclohexylamino)phenylphosphine as a PN2 ligand

Transition metal-catalyzed functionalization of pyrazines

“…An example of the amination of chloropyrazine was recently reported by Kim et al 63 Using Pd 2 (dba) 3 together with a bulky electron-rich phosphine ligand the corresponding phenylaminopyrazine was obtained in 59% yield (Scheme 39).…”

Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions

“…The enzymatic oxidation of nitrobenzene can synthesize meta -nitrophenol with excellent site-selectivity, although this method suffers from the poor generality of substrates [ 9 ]. In this regard, transition metal-catalyzed cross-coupling reactions using meta -haloanilines and meta -halophenols are among the most frequently employed methods ( Figure 2 b) [ 10 , 11 , 12 , 13 , 14 , 15 ]. For example, Buchwald–Hartwig amination reactions of meta -halophenol derivatives using palladium catalysts [ 10 , 11 , 12 , 13 ] and Ullman-type reactions using copper catalysts [ 14 , 15 ] have been frequently used for the synthesis of meta -aminophenol derivatives.…”

“…In this regard, transition metal-catalyzed cross-coupling reactions using meta -haloanilines and meta -halophenols are among the most frequently employed methods ( Figure 2 b) [ 10 , 11 , 12 , 13 , 14 , 15 ]. For example, Buchwald–Hartwig amination reactions of meta -halophenol derivatives using palladium catalysts [ 10 , 11 , 12 , 13 ] and Ullman-type reactions using copper catalysts [ 14 , 15 ] have been frequently used for the synthesis of meta -aminophenol derivatives. Catalytic C–O bond-forming reactions using meta -haloanilines have also been employed as an alternative approach to cross-coupling reactions by employing various transition metal catalysts, such as palladium [ 16 , 17 ], copper [ 18 , 19 ], nickel [ 20 ], and gold [ 21 ].…”

Diels–Alder Construction of Regiodifferentiated meta-Amino Phenols and Derivatives

“…They have proven themselves as privileged pharmaceutical scaffolds and serve as inhibitors of JNK and CGRP, modulators of the delta-opioid receptor, and efficacious treatment for neurological and psychiatric maladies, Alzheimer’s disease, and various carcinomas . However, differentially substituted m -APhOHs and m -APyOHs, particularly those displaying electron-deficient amino functionality, are tedious to construct by aryl nitration–reduction–protection regimes, palladium mediated cross-coupling sequences, and other strategies, such as conventional Diels–Alder sequences …”