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Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts.

ABSTRACT: A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

SUBMITTER: Kervefors G

PROVIDER: S-EPMC8048889 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts.

Kervefors Gabriella G Kersting Leonard L Olofsson Berit B

Chemistry (Weinheim an der Bergstrasse, Germany) 20210303 18

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The ...[more]

PMID: 33481266

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