Direct cross-coupling of alcohols with C-nucleophiles catalyzed by N-halosuccinimide under solvent-free reaction conditions
Organic Chemistry: Current Research

Organic Chemistry: Current Research
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ISSN: 2161-0401

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Direct cross-coupling of alcohols with C-nucleophiles catalyzed by N-halosuccinimide under solvent-free reaction conditions

10th European Organic Chemistry Congress

March 21-22, 2019 | Rome, Italy

Njomza Ajvazi and Stojan Stavber

Jozef Stefan International Postgraduate School, Slovenia Jozef Stefan Institute, Slovenia College of Medical Sciences ├ó┬?┬?Rezonanca├ó┬?┬Ł, Kosovo

Scientific Tracks Abstracts: Organic Chem Curr Res

Abstract :

Nucleophilic substitution of alcohols leading to the construction of the C-C bond following the principles of green chemistry has become an attractive process used in the synthesis of organic compounds. Because increasing numbers of organic solvents are restricted due to their damaging effects on human health and the environment, performing reactions under solvent-free reaction conditions (SFRC), have attracted significant interest in organic chemistry research and development because of their simplicity and cost efficiency. C-C bond construction reactions display one of the most important implements in synthetic organic chemistry since they provide access to pharmaceutically important molecules or agrochemicals. C-C bond construction by direct cross-coupling of alcohols with C-nucleophiles could be a desirable strategy offering a potential impact on the environment since water is the only by-product of the reaction. Hydroxyl functional group is one of the most abundant in organic compounds. In order to manipulate a specific transformation of a hydroxyl moiety, often its activation is necessary, but in some cases, its direct substitution is also possible. Numerous related methodologies have been elaborated employing a sub-stoichiometric amount of Bronsted acids, metals ions, Lewis/Bronsted acid combination or other promoters. However, these reactions involve either toxic or expensive reagents, environmentally undesirable solvents, a high concentration of the catalyst, prolonged reaction time or high temperature. Thus, the development of an efficient, selective and environmentally benign catalytic methodology for C-C bond construction remains an attractive research challenge. A group of organic molecules bearing an active N-halogen bond: N-halosuccinimides (chloro, bromo or iodo respectively), are an inexpensive, commercially available and metal-free reagents which are widely used in organic synthesis as oxidizing, hydroxy halogenating or halogenating agents. We report new, efficient and selective methodology for the direct cross-coupling of alcohols with C-nucleophiles catalyzed by N-halosuccinimide as metal-free catalyst under SFRC, enhancing the green chemical profiles of these transformations.

Recent Publications

1. Anastas P T and Warner J C (1998) Green Chemistry: Theory and Practice. Oxford University Press.

2. Tanaka K (2003) Solvent-free organic synthesis. Wiley.

3. Trost B M (2002) On Inventing Reactions for Atom Economy. Accounts of Chemical Research 35(9):695-705.

4. Ajvazi N and Stavber S (2016) Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions. Tetrahedron Letters 57(22):2430-2433.

5. Ajvazi N and Stavber S (2018) Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances. Arkivoc ii:288-329.

Biography :

Njomza Ajvazi has completed her BSc and MSc in the field of Organic Chemistry with Biochemistry at the University of Prishtina "Hasan Prishtina", Kosovo, in 2009. Her Doctor of Science degree was conferred by Jo├?┬żef Stefan International Postgraduate School, Ljubljana, Slovenia, in 2016, under the supervision of Professor Dr. Stojan Stavber. Currently, she is an Assistant Professor at the College of Medical Sciences "Rezonanca", and Teaching Assistant at the Faculty of Agriculture and Veterinary at the University of Prishtina "Hasan Prishtina", Kosovo. Her research interest is the development of new methodologies for comprehensive direct transformation of alcohols forming new C-C or C-heteroatom bonds under green reaction conditions.