Utility of pentachloropyridine in organic synthesis

• Published in: Journal of the Iranian Chemical Society Vol. 17; no. 9; pp. 2145 - 2178
• Main Authors: Ranjbar-Karimi, Reza, Davoodian, Tayebeh, Mehrabi, Hossein
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.09.2020; Springer Nature B.V
• Subjects: Analytical Chemistry; Biochemistry; Chemical compounds; Chemical synthesis; Chemistry; Chemistry and Materials Science; Heterocyclic compounds; Inorganic Chemistry; Organic Chemistry; Organic compounds; Physical Chemistry; Review; Pentachloropyridine; Perchloropyridine; Polysubstituted pyridine; Aromatic nucleophilic substitution; Macrocycle
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-020-01909-y

Pentachloropyridine is one of the most important perhalogenated compounds which find broad applications in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis, reaction and use of pentachloropyridine as building blocks in the synthesis of chemical relevant organic compounds. In the first part of the review, the different synthetic approaches of pentachloropyridine have been described. In the other part, an overview of the utility of pentachloropyridine into heterocyclic compounds, as well as other organic derivatives derived from pentachloropyridine, is presented. It has been shown in the literature that many factors including the nature of nucleophile, reaction condition, and solvent can have significant influences in the regiochemistry of the reactions of this heteroaromatic compound. Graphic abstract