Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation

Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation Научная публикация

Журнал

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Вых. Данные

Год: 2015, Том: 11, Страницы: 608-616 Страниц : DOI: 10.3762/bjoc.11.68

Ключевые слова

potassium polyfluoroaryltrifluoroborate; silver(I) acceleration; Suzuki-Miyaura reaction

Авторы

Bardin Vadim V. ^1,2 , Shabalin Anton Yu. ³ , Adonin Nicolay Yu. ^2,3

Организации

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

Small differences in the reactivity of weakly nucleophilic potassium aryltrifluoroborates are revealed in the silver-assisted Pd-catalyzed cross-coupling of K[4-RC6F4BF3] (R = H, Bu, MeO, EtO, PrO, iPrO, BuO, t-BuO, CH2=CHCH2O, PhCH2O, PhCH2CH2O, PhO, F, pyrazol-1-yl, pyrrol-1-yl, and indol-1-yl) with ArX (4-BrC6H4CH3, 4-IC6H4F and 3-IC6H4F). An assumed role of silver(I) compounds AgmY (Y = O, NO3, SO4, BF4, F) consists in polarization of the Pd-X bond in neutral complex ArPdLnX with the generation of the related transition state or formation of [ArPdLn][XAgmY] with a highly electrophilic cation and subsequent transmetallation with the weakly nucleophilic borate. Efficiency of AgmY as a polarizing agent decreases in order Ag2O > AgNO3 approximate to Ag2SO4 > Ag[BF4] > AgF. No clear correlation between the reactivity of K[4-RC6F4BF3] and substituent electron parameters, sigma(I) and sigma(R)degrees, of the aryl group 4-RC6F4 was found.

Bardin V.V. , Shabalin A.Y. , Adonin N.Y.
Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation

Beilstein Journal of Organic Chemistry. 2015. V.11. P.608-616. DOI: 10.3762/bjoc.11.68 WOS Scopus РИНЦ OpenAlex

Полный текст от издателя

Опубликована online:

4 мая 2015 г.

Web of science:	WOS:000353874400001
Scopus:	2-s2.0-84930655108
РИНЦ:	24045991
OpenAlex:	W348623969

БД	Цитирований
Web of science	17
Scopus	17
РИНЦ	17
OpenAlex	19