New Synthetic Applications of Aryllead Triacetates. N-Arylation of Amides

Abstract

p-Tolyllead triacetate efficiently arylates the nitrogen atom of carboxamide, sulfonamide, imide, and hydantoin anions under mild conditions. This reaction did not interfere with the arylation of amino and β-dicarbonyl groups.

N-arylation of imides with arylboronic acids using Cu-Al hydrotalcite

“…The N-arylation of NH-containing substrates is important in organic synthesis since the resultant products, arylamines and N-arylheterocycles are ubiquitous compounds in pharmaceuticals, crop protection chemicals and material sciences [1][2][3][4][5]. Hartwig [6], Buchwald and co-workers [7] and Shakespeare [8] reported the arylation of amines, amides and anilines with aryl halides using Pd/Ni catalysts.…”

“…Chan et al [9], Evans et al [10], Lam et al [11] and others [12] reported that arylamines and N-arylheterocycles can be prepared using boronic acids and cupric acetate [Cu(OAc) 2 ] under mild conditions compared to that of conventional Ullmann and Goldberg arylation protocols [13]. There are reports using arylsilanes [14], arylstannanes [11b], arylbismuth [15] and aryllead triacetates reagents [3] as aryl donors using cupric acetate in the presence of base. All these methods require stoichiometric amounts of Cu(OAc) 2 .…”

Nano CoCuFe2O4‐catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom‐economic and ligand‐free route to access unsymmetrical amines and sulfides

“…However, the development of mild and cost‐effective catalytic procedures for N‐arylation of amines and S‐arylation of thiols still remains an active research area. Aryl halide, aryllead, arylbismuth, arylborane and arylsilane compounds are used as coupling components for arylation reactions . Of these aryl surrogates, arylboronates are commercially available, non‐toxic, easily handled, and stable under air and moisture.…”

One-pot Synthesis and Dynamic Studies of Stable Dialkyl-2-(1H-Isoindol-1,3(2H)-dione-2-yl)-3-(Triphenylphosphoranylidene) Butanedioate ylides

“…Phthalimide is one of the longest known nitrogen heterocyclic compounds that has been used in the classical Gabriel procedure for the synthesis of amines. 1,2 Such methodology has found utility in the synthesis of wide variety of N-substituted alkyl, 3,4 aryl [5][6][7] and allyl 8,9 phthalimides. Some substituted phthalimides have demonstrated cytotoxicity 10 and anticancer properties.…”