Bis-Cyclometalated Indazole Chiral-at-Rhodium Catalyst for Asymmetric Photoredox Cyanoalkylations.
asymmetric catalysis
bis-cyclometalated
chiral-at-metal
metal-centered-chirality
photoredox catalysis
rhodium
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Dec 2019
02 Dec 2019
Historique:
received:
24
07
2019
revised:
02
09
2019
pubmed:
22
9
2019
medline:
22
9
2019
entrez:
22
9
2019
Statut:
ppublish
Résumé
A new class of bis-cyclometalated rhodium(III) catalysts containing two inert cyclometalated 6-tert-butyl-2-phenyl-2H-indazole ligands and two labile acetonitriles is introduced. Single enantiomers (>99 % ee) were obtained through a chiral-auxiliary-mediated approach using a monofluorinated salicyloxazoline. The new chiral-at-metal complex is capable of catalyzing the visible-light-induced enantioselective α-cyanoalkylation of 2-acyl imidazoles in which it serves a dual function as the chiral Lewis acid catalyst for the asymmetric radical chemistry and at the same time as the photoredox catalyst for the visible-light-induced redox chemistry (up to 80 % yield, 4:1 d.r., and 95 % ee, 12 examples).
Identifiants
pubmed: 31541505
doi: 10.1002/chem.201903369
pmc: PMC6916287
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15333-15340Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : ME1805/17-1
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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