A New Application of (Polyfluoroorgano)trifluoroborate Salts: The Palladium-Catalysed Cross-Coupling Reaction with Substituted Benzenediazonium Tetrafluoroborates | Sciact - CRIS-system of Boreskov Institute of Catalysis

A New Application of (Polyfluoroorgano)trifluoroborate Salts: The Palladium-Catalysed Cross-Coupling Reaction with Substituted Benzenediazonium Tetrafluoroborates Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2002, Volume: 117, Number: 2, Pages: 115-120 Pages count : 6 DOI: 10.1016/s0022-1139(02)00157-4

Tags

(Polyfluorophenyl)trifluoroborates; (Perfluoroethenyl)trifluoroborate; Benzenediazonium tetrafluoroborates; Pd-catalysis; Cross-coupling reactions; NMR spectroscopy

Authors

Frohn Hermann-Josef ¹ , Adonin Nicolay Yu. ² , Bardin Vadim V. ² , Starichenko Vladimir F. ²

Affiliations

1	Institute of Chemistry, Inorganic Chemistry, Gerhard-Mercator-University Duisburg, Lotharstr. 1, D-47048 Duisburg, Germany
2	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentjev Ave. 9, 630090 Novosibirsk, Russia

For the first time (polyfluoroorgano)trifluoroborate salts, namely K[C6F5BF3], K[C6HF4BF3] (all three isomers), K[3,4,5-C6H2F3BF3], and K[CF2=CFBF3] were principally applied as reagents to Pd-catalysed cross-coupling reactions. A series of polyfluorinated biphenyls C6H5−nFn–C6H4X-4′ were obtained from K[C6H5−nFnBF3] and the substrates [4-XC6H4N2][BF4] in the presence of Pd catalysts. The influence of the number and the position of the fluorine atoms in the (polyfluorophenyl)trifluoroborate salts on the reactivity in the coupling reaction was elucidated. In addition to (polyfluorophenyl)trifluoroborate salts, the cross-coupling was expanded to a first example of a perfluoroalkenyl reagent. K[CF2=CFBF3] reacted with [4-FC6H4N2][BF4] and formed CF2=CF–C6H4F-4. The cross-coupling reaction was successfully introduced into the synthesis of polyfluorophenyl and perfluoroethenyl derivatives of substituted benzenes.

Frohn H-J. , Adonin N.Y. , Bardin V.V. , Starichenko V.F.
A New Application of (Polyfluoroorgano)trifluoroborate Salts: The Palladium-Catalysed Cross-Coupling Reaction with Substituted Benzenediazonium Tetrafluoroborates
Journal of Fluorine Chemistry. 2002. V.117. N2. P.115-120. DOI: 10.1016/s0022-1139(02)00157-4 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Apr 22, 2002
Accepted:	May 10, 2002
Published online:	Sep 16, 2002
Published print:	Oct 1, 2002

Web of science:	WOS:000179152200006
Scopus:	2-s2.0-0037191005
Elibrary:	13393014
Chemical Abstracts:	2002:831300
Chemical Abstracts (print):	138:28731
OpenAlex:	W1983655940

DB	Citing
Scopus	53
Web of science	48
OpenAlex	53