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Protonated Phosphazenes: Structures and Hydrogen‐Bonding Organocatalysts for Carbonyl Bond Activation
Author(s) -
Jardel Damien,
Davies Clotilde,
Peruch Frédéric,
Massip Stéphane,
Bibal Brigitte
Publication year - 2016
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.201600062
Subject(s) - chemistry , steric effects , protonation , catalysis , monomer , hydrogen bond , polymer chemistry , polymerization , organocatalysis , ring (chemistry) , photochemistry , organic chemistry , combinatorial chemistry , molecule , polymer , enantioselective synthesis , ion
Abstract The synthesis and application of protonated phosphazeniums as hydrogen‐bond donor groups was demonstrated in the solid state and in solution. In particular, their catalytic activity was shown in the activation of the carbonyl group within cyclic esters, using a benchmark reaction, that is, in the ring‐opening polymerization of lactide and valerolactone, in the presence of a basic co‐catalyst. The reactions proceed differently depending on monomers and/or phosphazenium salts. The impact of catalysts and reactants steric hindrance upon the outcome of the reaction is then highlighted and discussed.