Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.
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.
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.|The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Saqib
S
Faisal
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.|The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Pradip K
PK
Maity
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.|The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Qin
Q
Zang
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.|The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Alan
A
Rolfe
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.|The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Paul R
PR
Hanson
D000477:Alkylating Agents / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009556:Niobium / Q000737:chemistry; D058105:Polymerization; D015203:Reproducibility of Results; D012822:Silicon Dioxide / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D000477:Alkylating Agents; D001593:Benzyl Compounds; D001880:Boranes; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D014230:Triazoles; D009556:Niobium; D012822:Silicon Dioxide
ROMP reagents; alkylating agents; hetero(triazolyl)methylation; heterobenzylation; silica-immobilized reagents