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Unprecedented Control of Selectivity in Nickel‐Catalyzed Hydrophosphorylation of Alkynes: Efficient Route to Mono‐ and Bisphosphonates
Author(s) -
Khemchyan Levon L.,
Ivanova Julia V.,
Zalesskiy Sergey S.,
Ananikov Valentine P.,
Beletskaya Irina P.,
Starikova Zoya A.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400123
Subject(s) - chemistry , catalysis , nickel , selectivity , combinatorial chemistry , scope (computer science) , atom economy , reaction conditions , reaction mechanism , atom (system on chip) , organic chemistry , computer science , embedded system , programming language
A unique nickel‐based catalytic system was developed where the direction of the hydrophosphorylation reaction can be controlled by varying the catalyst loading. A flexible one‐pot access to vinylmonophosphonates and alkylbisphosphonates was demonstrated using simple starting materials in an atom‐economic reaction without any specific solvents or ligands. Monitoring of the reaction mechanism with joint NMR and MS studies revealed key information about the reaction intermediates. The synthetic scope of the developed catalytic system was explored and the utility of the synthesized products for the fire protection of cotton materials was demonstrated.