Cobalt-Catalyzed C(sp2)–H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group

Organic Letters 2021
Lūkass Tomass Lukašēvics, A Cizikovs, Liene Grigorjeva

Herein we report an efficient protocol for the C(sp2)-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst. Carbonylation was accomplished using picolinamide as a traceless directing group, CO (1 atm) as the carbonyl source, and Co(dpm)2 as the catalyst. A broad range of phenylalanine derivatives bearing diverse functional groups were tolerated. Moreover, the method can be successfully applied for the C(sp2)-H carbonylation of short peptides thereby allowing access for peptide late-stage carbonylation.

Keywords
Amines; Amino Acids; Catalysis; Cobalt; Molecular Structure; Peptides; Picolinic Acids
DOI
10.1021/acs.orglett.1c00660
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.orglett.1c00660

Lukašēvics, L., Cizikovs, A., Grigorjeva, L. Cobalt-Catalyzed C(sp2)–H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group. Organic Letters, 2021, Vol. 23, No. 7, pp.2748-2753. ISSN 1523-7060. e-ISSN 1523-7052. Available from: doi:10.1021/acs.orglett.1c00660

Publication language
English (en)