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Magnetic Silyl Scaffold Enables Efficient Recycling of Protecting Groups
Author(s) -
Schaetz Alexander,
Zeltner Martin,
Michl Thomas D.,
Rossier Michael,
Fuhrer Roland,
Stark Wendelin J.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101165
Subject(s) - moiety , reagent , pyridine , silylation , copolymer , chemistry , scaffold , styrene , cobalt , durability , chemical engineering , polymer chemistry , catalysis , organic chemistry , combinatorial chemistry , materials science , composite material , polymer , biomedical engineering , medicine , engineering
A novel organic/inorganic hybrid material comprising carbon‐coated cobalt nanoparticles and a poly(benzylchloride)styrene shell is the first magnetic support that complies with important requirements for immobilized reagents and scavengers, that is, stability under harsh conditions (e.g., acids), sufficient loading (up to 2 mmol g −1 ), and satisfying magnetization. The durability of the scaffold was demonstrated by immobilization of a trialkylsilane reagent, which served as a “magnetic” protecting group for a number of primary and secondary alcohols. Importantly, the scaffold could be efficiently separated, recycled, and reused after alcohol cleavage (HF⋅pyridine) via regeneration of the silyl chloride moiety with BCl 3 .