B-Containing Hydrotalcites Effectively Catalyzed Synthesis of 3-(Furan-2-yl)acrylonitrile Derivatives via the Knoevenagel Condensation

5-Hydroxymethylfurfural (HMF) is a well-known platform chemical derivative from biomass. Herein, we described the application of boric acid deposited on hydrotalcite as a catalyst in the Knoevenagel reaction of HMF derivatives and active methylene compounds to afford new HMF derivatives containing an acrylonitrile moiety under solvent-free conditions. The boric acid incorporation method on hydrotalcite conditioned the yields obtained because the aluminum substitution by boron atoms can modify the acidity of these solids. The Knoevenagel adduct structure (3a) was studied and confirmed by X-ray crystallography. This protocol synthesis features operational simplicity, short reaction times, high yields, good to excellent (E)-isomer selectivity, and low catalyst loading. Remarkably, the catalyst could be simply recovered and reused up to five cycles without appreciable loss of catalytic activity. © 2022 American Chemical Society. All rights reserved.

Авторы
Mancipe S. , Castillo J.-C. , Brijaldo M.H. , López V.P. , Rojas H. , Macías M.A. , Portilla J. , Romanelli G.P. , Martínez J.J. , Luque R.
Издательство
American Chemical Society
Номер выпуска
38
Язык
Английский
Страницы
12602-12612
Статус
Опубликовано
Том
10
Год
2022
Организации
  • 1 Escuela de Ciencias Química-Grupo de Catálisis, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja, 150003, Colombia
  • 2 Escuela de Ciencias Administrativas y Economicas-Grupo de Investigacion de Farmacia y Medio Ambiente, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja, 150003, Colombia
  • 3 Crystallography and Chemistry of Materials, Department of Chemistry, Universidad de Los Andes, Carrera 1 No. 18A-10, Bogotá, 111711, Colombia
  • 4 Bioorganic Compounds Research Group, Department of Chemistry, Universidad de Los Andes, Carrera 1 No. 18A-10, Bogotá, 111711, Colombia
  • 5 Centro de Investigación y Desarrollo en Ciencias Aplicadas Dr. Jorge J. Ronco, Universidad Nacional de la Plata, Calle 47 No 257, La Plata, B1900AJK, Argentina
  • 6 Centro de Investigación en Sanidad Vegetal (CISaV), Cátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de la Plata, Calles 60 y 119 S/N, La Plata, B1904AAN, Argentina
  • 7 Departamento de Química Orgánica, Grupo FQM-383, Universidad de Córdoba, Campus Universitario de Rabanales, Edificio Marie Curie (C3), Córdoba, E-14014, Spain
  • 8 Peoples Friendship University of Russia, RUDN University, 6 Miklukho Maklaya Street, Moscow, 117198, Russian Federation
Ключевые слова
active methylene; boric acid; HMF; hydrotalcite; solvent free
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