Clean and molecularly programmable protocol for preparation of bis-heterobiarylic systems via a domino pseudocyclic reaction as a valuable alternative for TM-catalyzed cross-couplings
Authors:
- Przemysław Woliński,
- Agnieszka Kącka-Zych,
- Oleg M. Demchuk,
- Agnieszka Łapczuk-Krygier,
- Barbara Mirosław,
- Radomir Jasiński
Abstract
The domino sequence of pseudocyclic reactions involving 4-methoxybenzonitrile N-oxide and trans-2-phenyl-1-cyano-1-nitroethene proceeding in mild (r.t.; atm. pressure) non-catalytic (without participation of palladium or other transition metals (TM)) conditions yielded a bis-heterobiarylic molecular system containing an oxadiazole moiety with an almost 40% yield. The presented methodology represents therefore an evident contrast to the existing methods of preparation of bis-heterobiarylic systems, which require the presence of TMs. This reaction should be considered stereochemically “clean” and contains a stage of cycloaddition to the CN bond. It should be underlined that this is the first case of non-catalyzed [3 + 2] cycloaddition involving the nitrile CN bond. Our comprehensive study shows that the described protocol can be applied as a general methodology for preparation of a wide group of bis-heterobiarylic molecules. The self-adjusted cascade of transformations, which is unique and valuable from the practical point of view, leads to formation of a single isomeric product (from many possible) as a consequence of three pseudocyclic tandem reactions performed in agreement with the fundamental principles of green chemistry and sustainable development with a maximal level of atom economy and good overall yields. A self-adjustment phenomenon observed in the studied smart technology leading to production of a material with special properties was explained by it deep quantum nature confirmed undoubtedly by the modern Molecular Electron Density Theory.
- Record ID
- CUT50789c40ad774d9eaeb9f70e60294e1a
- Publication categories
- ;
- Author
- Journal series
- Journal of Cleaner Production, ISSN 0959-6526, e-ISSN 1879-1786
- Issue year
- 2020
- Vol
- 275
- Pages
- [1-14]
- Article number
- 122086
- Other elements of collation
- rys.; schem.; tab.; Bibliografia (na s.) - 12-14; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 275
- Keywords in English
- bis-heterobiaryls, catalyst-free approach, (3+2) cycloaddition, molecular electron density theory, smart technology, sustainable development
- DOI
- DOI:10.1016/j.jclepro.2020.122086 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/abs/pii/S0959652620321338 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 140
- Publication indicators
- Citation count
- 21
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT50789c40ad774d9eaeb9f70e60294e1a/
- URN
urn:pkr-prod:CUT50789c40ad774d9eaeb9f70e60294e1a
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.