Highly Efficient Asymmetric Aerobic Oxidative Coupling of 2-Naphthols in the Presence of Bioinspired Iron Aminopyridine Complexes | Sciact - CRIS-system of Boreskov Institute of Catalysis

Highly Efficient Asymmetric Aerobic Oxidative Coupling of 2-Naphthols in the Presence of Bioinspired Iron Aminopyridine Complexes Full article

Journal

Catalysis Communications
ISSN: 1566-7367 , E-ISSN: 1873-3905

Output data

Year: 2018, Volume: 104, Pages: 112-117 Pages count : 6 DOI: 10.1016/j.catcom.2017.10.025

Tags

Asymmetric catalysis, C–C bond formation, C–H activation, Dioxygen, Enzyme models, Iron

Authors

Tkachenko Nikolay V. ^1,2 , Lyakin Oleg Y. ^1,2 , Samsonenko Denis G. ^1,3 , Talsi Evgenii P. ^1,2 , Bryliakov Konstantin P. ^1,2

Affiliations

1	Novosibirsk State University, Pirogova 2, Novosibirsk, Russian Federation
2	Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk, Russian Federation
3	Nikolaev Institute of Inorganic Chemistry, Pr. Lavrentieva 3, Novosibirsk, Russian Federation

Funding (2)

1	Federal Agency for Scientific Organizations	0303-2016-0005
2	Russian Foundation for Basic Research	17-03-00991

For the first time, it has been shown that chiral bipyrrolidine derived bioinspired non-heme iron complexes of the types [LFeX2], [LFe(μ-O)2FeL][X]4, and [LFe(μ-O)(μ-OAc)FeL][X]2 (where L – aminopyridine ligand, X− = OTf−, SbF6 −, ClO4 −) are capable of efficiently conducting aerobic oxidative coupling of 2-naphthols in an asymmetric fashion, with formation of the corresponding enantiomerically enriched BINOLs (up to 56% ee) in good yields (up to 94% within 24 h), using as little as 1 mol% of the catalyst. The effect of ligand substitutents, solvent, counteranion, 2-naphthol structure, and oxygen pressure on the catalytic performance has been systematically examined.

Tkachenko N.V. , Lyakin O.Y. , Samsonenko D.G. , Talsi E.P. , Bryliakov K.P.
Highly Efficient Asymmetric Aerobic Oxidative Coupling of 2-Naphthols in the Presence of Bioinspired Iron Aminopyridine Complexes
Catalysis Communications. 2018. V.104. P.112-117. DOI: 10.1016/j.catcom.2017.10.025 WOS Scopus РИНЦ AN OpenAlex

Submitted:	Sep 30, 2017
Accepted:	Oct 27, 2017
Published online:	Oct 28, 2017
Published print:	Jan 1, 2018

Web of science:	WOS:000423244900023
Scopus:	2-s2.0-85032908764
Elibrary:	31111141
Chemical Abstracts:	2017:1788653
OpenAlex:	W2766319209

DB	Citing
Web of science	16
Scopus	16
Elibrary	16
OpenAlex	19