Open AccessSynthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si–OHBP) and Triazolyl Phosphate (Si–OHTP) Alkylating Reagents
Author(s) -
Saqib Faisal,
Pradip Maity,
Qin Zang,
Alan Rolfe,
Paul R. Hanson
Publication year - 2016
Publication title -
acs combinatorial science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.928
H-Index - 81
eISSN - 2156-8952
pISSN - 2156-8944
DOI - 10.1021/acscombsci.6b00042
Subject(s) - chemistry , reagent , phosphate , alkylation , combinatorial chemistry , yield (engineering) , monomer , nucleophile , silica gel , organic chemistry , catalysis , polymer , materials science , metallurgy
The development of new ROMP-derived silica-immobilized heterocyclic phosphate reagents and their application in purification-free protocols is reported. Grafting of norbornenyl norbornenyl-functionalized (Nb-tagged) silica particles with functionalized Nb-tagged heterocyclic phosphate monomers efficiently yield high-load, hybrid silica-immobilized oligomeric heterobenzyl phosphates (Si-OHBP) and heterotriazolyl phosphates (Si-OHTP) as efficient alkylation agents. Applications of these reagents for the diversification of N-, O-, and S-nucleophilic species, for efficient heterobenzylation and hetero(triazolyl)methylation have been validated.