Deaminative Arylation of Amino Acid-derived Pyridinium Salts.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
20 09 2019
20 09 2019
Historique:
pubmed:
30
8
2019
medline:
29
7
2020
entrez:
30
8
2019
Statut:
ppublish
Résumé
A Suzuki-Miyaura cross-coupling of α-pyridinium esters and arylboroxines has been developed. Combined with formation of the pyridinium salts from amino acid derivatives, this method enables amino acid derivatives to be efficiently transformed into α-aryl esters and amides. Under the mild conditions, broad functional group tolerance on both the amino acid derivatives and the arylboroxine are observed, including protic functional groups. Mechanistic studies support an alkyl radical intermediate, similar to other cross-couplings of alkylpyridinium salts.
Identifiants
pubmed: 31464131
doi: 10.1021/acs.orglett.9b02643
pmc: PMC6894616
mid: NIHMS1050277
doi:
Substances chimiques
Amides
0
Amino Acids
0
Boron Compounds
0
Esters
0
Pyridines
0
Salts
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
7356-7360Subventions
Organisme : NIH HHS
ID : S10 OD016267
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM111820
Pays : United States
Organisme : NIGMS NIH HHS
ID : P20 GM103541
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM131816
Pays : United States
Organisme : NIGMS NIH HHS
ID : P20 GM104316
Pays : United States
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