Сибирский федеральный университет

Тип публикации: статья из журнала

Год издания: 2020

Ключевые слова: brønsted acid catalyst, charge-assisted hydrogen-bonded framework, diels–alder, epoxide ring opening, heterogeneous catalyst

Аннотация: The acid-base neutralization reaction of commercially available disodium 2,6-naphthalenedisulfonate (NDS, 2 equivalents) and the tetrahydrochloride salt of tetrakis(4-aminophenyl)methane (TAPM, 1 equivalent) in water gave a novel three-dimensional charge-assisted hydrogen-bonded framework (CAHOF, F-1). The framework F-1 was characterized by X-ray diffraction, TGA, elemental analysis, and H-1 NMR spectroscopy. The framework was supported by hydrogen bonds between the sulfonate anions and the ammonium cations of NDS and protonated TAPM moieties, respectively. The CAHOF material functioned as a new type of catalytically active Bronsted acid in a series of reactions, including the ring opening of epoxides by water and alcohols. A Diels-Alder reaction between cyclopentadiene and methyl vinyl ketone was also catalyzed by F-1 in heptane. Depending on the polarity of the solvent mixture, the CAHOF F-1 could function as a purely heterogeneous catalyst or partly dissociate, providing some dissolved F-1 as the real catalyst. In all cases, the catalyst could easily be recovered and recycled.

Журнал: Beilstein journal of organic chemistry

Выпуск журнала: Vol. 16

Номера страниц: 1124-1134

ISSN журнала: 18605397

Место издания: Frankfurt am Main

Издатель: Beilstein-institut

• Kuznetsova Svetlana A.
• Gak Alexander S.
• Nelyubina Yulia V.
• Larionov Vladimir A. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; Peoples Friendship Univ Russia, RUDN Univ, Dept Inorgan Chem, Miklukho Maklaya St 6, Moscow 117198, Russia)
• Li Han (Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England)
• North Michael (Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England)
• Zhereb Vladimir P. (Siberian Fed Univ, Sch Nonferrous Met & Mat Sci, 95 Krasnoyarskiy Rabochiy Pr, Krasnoyarsk 660025, Russia)
• Smol'yakov Alexander F. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)
• Dmitrienko Artem O. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)
• Medvedev Michael G. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; ND Zelinsky Inst Organ Chem RAS, Leninsky Prospect 47, Moscow 119991, Russia)
• Gerasimov Igor S. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; ND Zelinsky Inst Organ Chem RAS, Leninsky Prospect 47, Moscow 119991, Russia)
• Saghyan Ashot S. (Yerevan State Univ, Inst Pharm, 1 Alex Manoogian Str, Yerevan 0025, Armenia )
• Belokon Yuri N. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)

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