[reaction: see text] The addition of aryl- and heteroarylboronic acids to azo compounds is described. Copper salt catalysis was necessary to perform the reaction under mild conditions and high yields. Excellent regioselectivity was observed in addition to unsymmetrical azo compounds.
Structural and electronic features that facilitate and direct the intramolecular C- and N-arylation of 2-alkyl-2-{[N-(benzyl)-2-nitrophenyl]sulfonamido}acetic acid esters and amides were examined. The substitution pattern and amino acid carboxy-terminal functionality determined the arylation position. C/N-arylated products represent advanced intermediates for combinatorial synthesis of diverse nitrogenous heterocycles, including indazoles, quinazolinones, quinoxalinones, and 3-amino-2-oxindoles.
N-Benzyl-2-nitrobenzenesulfonamides underwent base-mediated intramolecular arylation at the benzyl sp(3) carbon to yield benzhydrylamines. The presence of electron withdrawing groups on the aromatic ring of the benzyl group was required to facilitate the C-arylation. Unsymmetrically substituted benzhydrylamines are advanced intermediates toward nitrogenous heterocycles, as exemplified in the syntheses of indazole oxides and quinazolines.
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