Palladium Catalyzed C(sp3)–H Trifluoroethoxylation | Sciact - CRIS-system of Boreskov Institute of Catalysis

Palladium Catalyzed C(sp3)–H Trifluoroethoxylation Full article

Journal

Journal of Catalysis
ISSN: 0021-9517 , E-ISSN: 1090-2694

Output data

Year: 2024, Volume: 435, Article number : 115563, Pages count : 5 DOI: 10.1016/j.jcat.2024.115563

Tags

Alkoxylation; Alternative rebound; C–H activation; Heterofunctionalization; Palladium; Selective oxidation

Authors

Lubov Dmitry P. ¹ , Ivanov Konstantin S. ² , Nefedov Andrey A. ^2,3 , Talsi Evgenii P. ¹ , Bryliakov Konstantin P. ⁴

Affiliations

1	Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russia
2	Novosibirsk State University, Pirogova 1, Novosibirsk 630090, Russia
3	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Lavrentieva 9, Novosibirsk 630090, Russia
4	Zelinsky Institute of Organic Chemistry RAS, Leninsky Pr. 47, Moscow 119991, Russia

Funding (3)

1	Ministry of Science and Higher Education of the Russian Federation	FWUR-2024-0032
2	The Ministry of Education and Science of the Russian Federation
3	Ministry of Science and Higher Education of the Russian Federation

Palladium(II) complexes of the TPA family (TPA − tris(2-pyridylmethyl)amine) have recently emerged as efficient catalysts of highly 3°-regioselective hydroxylation and chemoselective 2°-ketonization of aliphatic C–H groups with peroxycarboxylic acids. Herewith, we present a novel facet of the catalytic reactivity of such complexes that have been shown to mediate highly efficient (at as low as 0.6 mol. % catalyst loadings) and selective trifluoroethoxylation of organic substrates at benzylic C–H groups, affording the corresponding trifluoroethoxy ethers in up to 73 % isolated yield. The developed synthetic protocol allows for diastereoselective trifluoroethoxylation of complex molecules of natural origin (steroids, terpenoids).

Lubov D.P. , Ivanov K.S. , Nefedov A.A. , Talsi E.P. , Bryliakov K.P.
Palladium Catalyzed C(sp3)–H Trifluoroethoxylation
Journal of Catalysis. 2024. V.435. 115563 :1-5. DOI: 10.1016/j.jcat.2024.115563 WOS Scopus РИНЦ AN OpenAlex

Submitted:	Apr 9, 2024
Accepted:	May 17, 2024
Published online:	May 18, 2024
Published print:	Jul 1, 2024

Web of science:	WOS:001247322700001
Scopus:	2-s2.0-85194074356
Elibrary:	67803853
Chemical Abstracts:	2024:1171451
OpenAlex:	W4397032446

DB	Citing
Scopus	1
OpenAlex	1
Web of science	1