Journal
ORGANIC LETTERS
Volume 23, Issue 7, Pages 2748-2753Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00660
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Funding
- Latvian Council of Science, project [Cobalt catalyzed C-H bond functionalization] [lzp-2019/1-0220]
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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.
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.
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