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

Herein we report an efficient protocol for the C(sp(2))-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(sp(2))-H carbonylation of short peptides thereby allowing access for peptide late-stage carbonylation.

Automated summary

An efficient protocol for the C(sp(2))-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst is reported. The method utilizes picolinamide as a traceless directing group and Co(dpm)(2) as the catalyst, allowing for a broad range of phenylalanine derivatives bearing diverse functional groups to be tolerated. Moreover, the method can be successfully applied for the C(sp(2))-H carbonylation of short peptides, enabling access for peptide late-stage carbonylation.