Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.
Oxidative coupling
cross-coupling
phenol coupling
photocatalysis
tyrosine dimerization
Journal
ACS catalysis
ISSN: 2155-5435
Titre abrégé: ACS Catal
Pays: United States
ID NLM: 101562209
Informations de publication
Date de publication:
18 Dec 2020
18 Dec 2020
Historique:
entrez:
30
4
2021
pubmed:
1
5
2021
medline:
1
5
2021
Statut:
ppublish
Résumé
The oxidative photocatalytic method for phenol-phenol homo-coupling and cross-coupling is described and isolated yields of 16-97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters support a mechanism of nucleophilic attack of one partner onto the oxidized neutral radical form of the other partner. Understanding of this model permitted development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols with high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, a non-enzymatic, catalytic method for coupling tyrosine was also developed.
Identifiants
pubmed: 33927912
doi: 10.1021/acscatal.0c04515
pmc: PMC8078885
mid: NIHMS1669417
doi:
Types de publication
Journal Article
Langues
eng
Pagination
14615-14623Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM131902
Pays : United States
Organisme : NIH HHS
ID : S10 OD011980
Pays : United States
Organisme : NCRR NIH HHS
ID : S10 RR022442
Pays : United States
Organisme : NCRR NIH HHS
ID : S10 RR023444
Pays : United States
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