Copper‐Promoted N‐Arylation of the Indole Side Chain of Tryptophan Using Triarylbismuthines

Abstract

A simple protocol for the regioselective N-arylation of the indole side chain of tryptophan using triarylbismuth reagents as the arylating agent is reported. The reaction is catalyzed by copper(II) acetate, and operates in the presence of triethylamine or pyridine under air at 50°C. This reaction allows [a]

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

“…However, to the best of our knowledge, organobismuth reagents have never been used for the arylation of the side chain of amino acids. Recently, we reported a protocol for the N‐arylation of the indole side chain of tryptophan that operates directly from triarylbismuth reagents . We now report our results on the copper‐promoted O‐arylation of the side chain of tyrosine using functionalized triarylbismuthines (Scheme b ).…”

Late-stage peptide modification and macrocyclization enabled by tertiary amine catalyzed tryptophan allylation

“…A copper-promoted N (in) -arylation of the indole ring of Trp with triarylbismuthine species has been reported by Gagnon and coworkers. 40 More recently, Paixão and coworkers have disclosed the dual photoredox/metal catalysis mediated N (in) -arylation of tryptophan-containing peptide on resin. 41 Our group has developed a chiral phosphoric acid-catalyzed chemospecific enantioselective functionalization of tryptophan at the N1 position, enabling direct access to chiral propargyl aminal derivatives with good yields and stereoselectivities.…”