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Effect of Salt and Phosphine Additives on the Composition of Active Palladium Complexes in the Mizoroki-Heck Reaction with Aromatic Carboxylic Anhydrides Научная публикация

Журнал Kinetics and Catalysis
ISSN: 0023-1584 , E-ISSN: 1608-3210
Вых. Данные Год: 2022, Том: 63, Номер: 2, Страницы: 207-217 Страниц : 11 DOI: 10.1134/S0023158422020057
Авторы Larina E.V. , Kurokhtina A.A. , Lagoda N.A. , Schmidt A.F.
Организации
1 Irkutsk State University, Chemical Department, 664003, Irkutsk, Russia
Реферат: This paper presents the results of studies on changes in the composition of palladium complexes responsible for the activation of substrates in the Mizoroki–Heck reaction between aromatic acid anhydrides and alkenes. The differential selectivity of the reaction under conditions of competition between a pair of anhydrides or alkenes indicates the catalytic activity of palladium complexes, the composition of which varies depending on the concentration ratio of a tertiary phosphine, an alkali metal halide used as a promoting additive, and a palladium catalyst precursor loaded into the system. It was found that, when the threshold values of the concentrations ratio between halide ions and the tertiary phosphine were achieved, only phosphine-free palladium complexes containing halide anions in their coordination sphere made a decisive contribution to the formation of reaction products in spite of the presence of phosphine in the system. At the same time, when a halide salt was present in low concentrations or absent at all, active Pd complexes could include tertiary phosphine (in phosphine-containing catalytic systems) and solvent molecules and aromatic carboxylate anions formed as a result of the conversion of the initial anhydride. Under the “noncompetitive” conditions of the Mizoroki–Heck reaction, it was found that the nature of the cation and anion of a halide salt added to the catalytic system had a key effect on the differential selectivity of the formation of a classical “Heck” product of alkene arylation and a carbonyl product (chalcone) formed through the parallel reaction pathway. It was demonstrated that the differential selectivity and the yield of the carbonyl-containing reaction product increased when bromide salt additives were used. Therefore, in principle, it is possible to control the composition of active palladium complexes responsible for the selective formation of various products in the Mizoroki–Heck reaction with aromatic acid anhydrides.
Библиографическая ссылка: Larina E.V. , Kurokhtina A.A. , Lagoda N.A. , Schmidt A.F.
Effect of Salt and Phosphine Additives on the Composition of Active Palladium Complexes in the Mizoroki-Heck Reaction with Aromatic Carboxylic Anhydrides
Kinetics and Catalysis. 2022. V.63. N2. P.207-217. DOI: 10.1134/S0023158422020057 WOS Scopus РИНЦ CAPlus OpenAlex
Оригинальная версия: Ларина Е.В. , Курохтина А.А. , Лагода Н.А. , Шмидт А.Ф.
Влияние добавок солей и фосфинов на состав активных комплексов палладия в реакции Мицороки–Хека с ангидридами ароматических кислот
Кинетика и катализ. 2022. Т.63. №2. С.234-246. DOI: 10.31857/S0453881122020058 РИНЦ
Даты:
Поступила в редакцию: 27 июл. 2021 г.
Принята к публикации: 27 сент. 2021 г.
Опубликована в печати: 1 апр. 2022 г.
Опубликована online: 16 мая 2022 г.
Идентификаторы БД:
Web of science: WOS:000796501300009
Scopus: 2-s2.0-85130281496
РИНЦ: 48585526
Chemical Abstracts: 2022:1305763
OpenAlex: W4280582013
Цитирование в БД:
БД Цитирований
Web of science 5
Scopus 5
OpenAlex 5
Альметрики: