The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl)

The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl) Научная публикация

Журнал

Tetrahedron
ISSN: 0040-4020

Вых. Данные

Год: 2014, Том: 70, Номер: 23, Страницы: 3720-3725 Страниц : DOI: 10.1016/j.tet.2014.04.019

Ключевые слова

Cross-coupling; Palladium catalyst; Bulky phosphine; Polyfluorinated organotrifluoroborates; Aryl halides

Авторы

Shabalin Anton Yu. ¹ , Adonin Nicolay Yu. ¹ , Bardin Vadim V. ^1,2 , Parmon Valentin N. ¹

Организации

1	(Данные Web of science) SB RAS, GK Boreskov Inst Catalysis, Novosibirsk 630090, Russia
2	(Данные Web of science) SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

The influence of the ligand nature on catalytic activity of palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate, which imitates the behavior of electron-deficient organoboron reagents, with aryl halides, ArHal (Hal=Br, Cl) was studied. The activity of the catalysts generated in situ from Pd(OAc)(2) and appropriate phosphorous containing ligands and the reaction selectivity was found to depend on the nature of bulky phosphines used as ligands. As a result, conditions for involving the electron-deficient organoboron reagent-potassium pentafluorophenyltrifluoroborate in the palladium-catalyzed cross-coupling with aryl bromides and aryl chlorides were identified. It was demonstrated that the chosen conditions are appropriate for the reaction of K[C6F5BF3] with benzyl chloride and benzyl bromide deriving pentafluorophenylarylmethanes, C6F5CH2Ar. (C) 2014 Elsevier Ltd. All rights reserved.

Shabalin A.Y. , Adonin N.Y. , Bardin V.V. , Parmon V.N.
The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl)
Tetrahedron. 2014. V.70. N23. P.3720-3725. DOI: 10.1016/j.tet.2014.04.019 WOS Scopus РИНЦ

Опубликована в печати:

1 июн. 2014 г.

Web of science	WOS:000336191600011
Scopus	2-s2.0-84899965937
РИНЦ	21877201
OpenAlex	W2950267769