Journal
ACS CATALYSIS
Volume 7, Issue 1, Pages 907-911Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03215
Keywords
photoredox catalysis; N-heteroarenes; decarboxylation; alpha-aminoalkylation; N-(acyloxy)phthalimide
Categories
Funding
- 973 Program [2012CB215305]
- NSFC [21325208, 21402181, 21572212]
- IPDFHCPST [2014FXCX006]
- CAS [KFJ-EW-STS-051, YZ201563]
- FRFCU
- PCSIRT
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An iridium photoredox catalyst in combination with a phosphoric acid catalyzes the decarboxylative alpha-aminoalkylation of natural and unnatural alpha-amino acid-derived redox-active esters (N-hydroxyphthalimide esters) with a broad substrate scope of N-heteroarenes at room temperature under irradiation. Dipeptide- and tripeptide-derived redox-active esters are also amenable substrates to achieve decarboxylative insertion of a N-heterocycle at the C-terminal of peptides, yielding molecules that have potential medicinal applications. The key factors for the success of this reaction are the following: use of a photoredox catalyst of suitable redox potential to controllably generate alpha-aminoalkyl radicals, without overoxidation, and an acid cocatalyst to increase the electron deficiency of N-heteroarenes.
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