Synthesis of Meta-substituted aniline derivatives by nucleophilic substitution

Highly Reactive, General, and Long‐Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles

“…[1][2][3][4] Although current catalysts are capable of coupling a wide range of amines with aryl halides, reactions with these catalysts have several limitations: the catalysts have short lifetimes in the reactions of primary amines with chloroarenes, even when conducted with the most recently developed, highly active catalysts containing basic, hindered alkylmonophosphines; [5][6][7][8][9][10][11][12][13][14][15] the reactions of primary alkyl amines with heteroaryl chloride reagents, which are important for the synthesis of biologically active molecules, have limited scope and require large amounts of catalyst; [7,8,11,13,[15][16][17][18][19][20] and the reactions of primary alkyl amines with chloroarenes that possess common protic functional groups have not been described.We now report on catalysts that can overcome these limitations. Our approach, which is based upon the selection of ligands that combine steric hindrance, strong electron donation, and tight chelation, leads to a catalyst that simultaneously possesses long lifetimes and displays high activity for reactions of primary nitrogen nucleophiles with chloropyridines.…”

Development of indazolylpyrimidine derivatives as high-affine EphB4 receptor ligands and potential PET radiotracers

“…31 Next, 3,5-di(morpholino)aniline 9 as second substructure (part B) was synthesized from the respective nitro compound as pointed out in the literature. 23,32 Crystals of 9 suitable for a single crystal X-ray analysis were grown from a saturated ethyl acetate/petroleum ether solution and the molecular structure was expressed in Figure 5. 31 Finally, two reactions paths were figured out for the connection of substructures A (7a-d and 8a-c) with B (compound: 9).…”

Synthesis of tertiary aryl amines of various aryl halides and secondary amines using ortho‐palladated complex of tribenzylamine

“…[1] The palladiumcatalyzed cross-coupling of amines with aryl halides has become a principal method for the formation of C-N bonds in aromatic systems. [2][3][4][5][6][7][8][9][10] Generally, the combination of palladium catalysts with various phosphine ligands and also N-heterocyclic carbenes results in excellent yields and high efficiency in cross-coupling reactions. However, most phosphine ligands are air and moisture sensitive, and economically and environmentally undesirable due to difficulties with their recovery and the formation of toxic phosphines as by-products in these reactions.…”

“…In addition, these compounds are important for the preparation of new ligands, artificial dyes, polymers, electronic materials and xerographic materials . The palladium‐catalyzed cross‐coupling of amines with aryl halides has become a principal method for the formation of C―N bonds in aromatic systems . Generally, the combination of palladium catalysts with various phosphine ligands and also N ‐heterocyclic carbenes results in excellent yields and high efficiency in cross‐coupling reactions.…”