Synthesis of K[4-ROC6F4BF3] from Potassium Pentafluorophenyltrifluoroborate and O-Nucleophiles | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthesis of K[4-ROC6F4BF3] from Potassium Pentafluorophenyltrifluoroborate and O-Nucleophiles Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2013, Volume: 149, Pages: 82-87 Pages count : 6 DOI: 10.1016/j.jfluchem.2013.01.020

Tags

NMR spectroscopy, Nucleophilic substitution, O-nucleophile, Pentafluorophenyltrifluoroborate

Authors

Shabalin Anton Yu. ¹ , Adonin Nicolay Yu. ¹ , Bardin Vadim V. ^1,2 , Prikhodʹko Sergey A. ¹ , Timofeeva Maria N. ¹ , Bykova Maria V. ¹ , Parmon Valentin N. ¹

Affiliations

1	G.K. Boreskov Institute of Catalysis, SB RAS, Acad. Lavrentjev Avenue 5, 630090 Novosibirsk, Russian Federation
2	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentjev Avenue 9, 630090 Novosibirsk, Russian Federation

Funding (1)

The Ministry of Education and Science of the Russian Federation

2012-1.2.1-12-000-1004-038

A new route to potassium polyfluoroaryltrifluoroborates, K[4-ROC6F4BF3], consisting in the nucleophilic alkoxydefluorination of K[C6F5BF3] with MOR (M = K, Na) in a polar aprotic solvent is suggested. Reaction of K[C6F5BF3] with KO-t-Bu proceeds smoothly at 25 degrees C in DME, but the attempted alkoxydefluorination of K[C6F5BF3] with other NaOR at 30 degrees C in DME failed. A series of K[4-ROC6F4BF3] (R approximate to Me, Et, Pr, i-Pr, Bu, PhCH2) is prepared using the corresponding sodium alkoxides in DMF at 130 degrees C in 80-90% isolated yield. Salt K[4-CH2=CHCH2OC6F4BF3] is prepared at 100 degrees C whereas at 130 degrees C formation of 2,3,5,6-C6F4HOCH2CH=CH2 occurs. Salt K[4-PhOC6F4BF3] is obtained in 82% yield using KOPh (2 equivalents) in DMSO at 130 degrees C.

Shabalin A.Y. , Adonin N.Y. , Bardin V.V. , Prikhodʹko S.A. , Timofeeva M.N. , Bykova M.V. , Parmon V.N.
Synthesis of K[4-ROC6F4BF3] from Potassium Pentafluorophenyltrifluoroborate and O-Nucleophiles
Journal of Fluorine Chemistry. 2013. V.149. P.82-87. DOI: 10.1016/j.jfluchem.2013.01.020 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Dec 14, 2012
Accepted:	Jan 23, 2013
Published online:	Feb 9, 2013
Published print:	May 1, 2013

Web of science:	WOS:000317883600013
Scopus:	2-s2.0-84875428391
Elibrary:	20428290
Chemical Abstracts:	2013:336402
Chemical Abstracts (print):	158:503989
OpenAlex:	W2080025051

DB	Citing
Web of science	13
Scopus	13
Elibrary	11
OpenAlex	13