Preparation of Heptafluoronaphthyllithiums and -Magnesiums: An Unexpected Difference in the Reactivity of Isomers C10F7H and C10F7Br Towards Organolithium and Organomagnesium Compounds | Sciact - CRIS-system of Boreskov Institute of Catalysis

Preparation of Heptafluoronaphthyllithiums and -Magnesiums: An Unexpected Difference in the Reactivity of Isomers C10F7H and C10F7Br Towards Organolithium and Organomagnesium Compounds Full article

Journal

Journal of Organometallic Chemistry
ISSN: 0022-328X

Output data

Year: 2019, Volume: 899, Article number : 120889, Pages count : 10 DOI: 10.1016/j.jorganchem.2019.120889

Tags

Alkyllithium; Bromoheptafluoronaphthalene; Ethylmagnesium bromide; Heptafluoronaphthalene; Metalation; Trimethylsilylheptafluoronaphthalene

Authors

Shmakov Mikhail M. ^1,2 , Bardin Vadim V. ^2,3 , Prikhod'ko Sergey A. ^1,2 , Adonin Nicolay Yu. ^1,2

Affiliations

1	Boreskov Institute of Catalysis, SB RAS, Acad. Lavrentiev Ave. 5, Novosibirsk, 630090, Russian Federation
2	Novosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russian Federation
3	Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentiev Ave. 9, Novosibirsk, 630090, Russian Federation

Funding (2)

1	Russian Foundation for Basic Research	16-29-10762
2	Ministry of Science and Higher Education of the Russian Federation	ГЗ-2017-2020

Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi. © 2019

Shmakov M.M. , Bardin V.V. , Prikhod'ko S.A. , Adonin N.Y.
Preparation of Heptafluoronaphthyllithiums and -Magnesiums: An Unexpected Difference in the Reactivity of Isomers C10F7H and C10F7Br Towards Organolithium and Organomagnesium Compounds
Journal of Organometallic Chemistry. 2019. V.899. 120889 :1-10. DOI: 10.1016/j.jorganchem.2019.120889 WOS Scopus РИНЦ AN OpenAlex

Submitted:	Feb 27, 2019
Accepted:	Aug 8, 2019
Published online:	Aug 11, 2019
Published print:	Oct 30, 2019

Web of science:	WOS:000485104600018
Scopus:	2-s2.0-85070596364
Elibrary:	41626595
Chemical Abstracts:	2019:1621285
OpenAlex:	W2967366388

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