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Synthesis of α ‐Hydroxyphosphonates Containing Functionalized 1,2,3‐Triazoles
Author(s) -
Lima Yanka R.,
Da Costa Gabriel P.,
Xavier Maurício C. D. F.,
De Moraes Maiara C.,
Barcellos Thiago,
Alves Diego,
Silva Márcio S.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003761
Subject(s) - moiety , steric effects , amide , chemistry , reagent , combinatorial chemistry , ketone , substrate (aquarium) , catalysis , triazole , solvent , organic chemistry , oceanography , geology
Herein, we described a simple and efficient protocol for the synthesis of α ‐hydroxyphosphonates containing 1,2,3‐triazole moiety in their structures under mild conditions. This approach was performed by Abramov reaction in a solvent‐free system, using Na 2 CO 3 as catalyst at 70 °C, which provided the desired products from moderate to excellent yields. The substrate scope was effective for different organic functions, such as ester, ketone, and amide. The synthetic route is modulated by the presence of a bulky group at the hydrophosphoryl reagent, avoiding steric hindrance, since the Abramov reaction can be approached before the Click‐Chemistry protocol. The synthesis can also be carried out in a one‐pot method, minimizing costs, and without side reactions. Additionally, the chiral discrimination of the synthesized products was easily accessed by 1 H and 31 P nuclear magnetic resonance experiments, using a chiral solvating agent.