Nucleophilic substitution of hydrogen in pyridine and its derivatives by organophosphorus nucleophiles in the presence of electron-deficient acetylenes
- Authors: Telezhkin A.A1, Volkov P.A1, Khrapova K.O1
-
Affiliations:
- A.E. Favorskii Irkutsk institute of chemistry SB RAS
- Issue: Vol 59, No 10 (2023)
- Pages: 1269-1300
- Section: Articles
- URL: https://journals.rcsi.science/0514-7492/article/view/247238
- DOI: https://doi.org/10.31857/S0514749223100026
- EDN: https://elibrary.ru/OLUKEL
- ID: 247238
Cite item
Abstract
The review considers publications on a new easy functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine, phenanthridine) by the electron-deficient acetylene (esters of acetylenecarboxylic acids, acylacetylenes, cyanoacetylenes)/P-nucleophile (phosphine chalcogenides, H -phosphonates) system. Particular attention is paid to the SN H reaction of regioselective cross-coupling of pyridines with secondary phosphine chalcogenides, initiated by acylacetylenes and leading to the formation of 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as trimodal adjuvants by (1) activating the pyridine ring towards P-nucleophiles, (2) deprotonating the P-H bond, and (3) facilitating the nucleophilic addition of the P-centered anion to the heterocyclic fragment, followed by the release of selectively reduced (to E -alkenes) acetylenes.
About the authors
A. A Telezhkin
A.E. Favorskii Irkutsk institute of chemistry SB RAS
P. A Volkov
A.E. Favorskii Irkutsk institute of chemistry SB RAS
Email: volkov_p_a@irioch.irk.ru
K. O Khrapova
A.E. Favorskii Irkutsk institute of chemistry SB RAS
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