Site-Selective γ-C(sp3 )-H and γ-C(sp2 )-H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group

Hua Lin; Chao Wang; Thomas D Bannister; Theodore M Kamenecka

doi:10.1002/chem.201802465

Site-Selective γ-C(sp³ )-H and γ-C(sp² )-H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group

Chemistry. 2018 Jul 5;24(38):9535-9541. doi: 10.1002/chem.201802465. Epub 2018 Jun 6.

Authors

Hua Lin¹, Chao Wang², Thomas D Bannister², Theodore M Kamenecka¹

Affiliations

¹ Department of Molecular Medicine, The Scripps Research Institute, Jupiter, Florida, 33458, USA.
² Department of Chemistry, The Scripps Research Institute, Jupiter, Florida, 33458, USA.

PMID: 29775502
DOI: 10.1002/chem.201802465

Abstract

The first selective Pd^II -catalysed γ-C(sp³ )-H and γ-C(sp² )-H arylation of free amino esters using a commercially available catalytic transient directing group. A variety of free amino esters, including α-amino esters and β-amino esters, amino monoesters and amino bis-esters, are shown to react with a diverse range of simple aryl and heteroaryl iodide reagents.

Keywords: C−H arylation; directing groups; free amino esters; palladium; unnatural amino acids.