A facile and practical copper diacetate mediated, ligand free C–N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes

Abstract

In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions.

Recent Progress Concerning the N-Arylation of Indoles

“…The tryptophan derivative S30-2a was also prepared using this procedure. In addition, a series of heteroatom arylations by organobismuth reagents has been reported [ 145 , 146 , 147 , 148 ].…”

Copper‐Promoted O‐Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines

“…Results show that N ‐Boc tryptophan methyl ester is as reactive as N ‐Boc tyrosine methyl ester and that N ‐Boc cysteine and histidine methyl esters are the third and fourth most reactive amino acids ( 3a , 4 – 6 ). The high reactivity of N‐protected tryptophan, cysteine and histidine is easily explained by the fact that triarylbismuthines are very efficient at arylating indoles,[12b] thiols and imidazoles N‐Protected serine, lysine and glutamine were much less reactive under these conditions ( 7 – 9 ). These results are somewhat surprising since 1,2‐amino alcohols,[12c] amines and amides can all be arylated efficiently with triarylbismuthines.…”

Ammonia surrogates in the synthesis of primary amines

“…Phthalimides, in general, serve as efficient surrogates for ammonia in various synthetic applications. Additional examples include their use in Ullmann-type reactions, 20 coupling with trivalent organobismuth reagents and copper salts, 21 coupling with boronic acids in Chan–Lam aminations, 22 and even visible light-induced C–H imidations 23 (Fig. 4).…”