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Neighboring Acetal‐Assisted Brønsted‐Acid‐Catalyzed Si–H Bond Activation: Divergent Synthesis of Functional Siloxanes through Silylation and Hydrolytic Oxidation of Organosilanes
Author(s) -
Chen XiHuai,
Deng Yuan,
Jiang Kezhi,
Lai GuoQiao,
Ni Yong,
Yang KeFang,
Jiang JianXiong,
Xu LiWen
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001532
Subject(s) - chemistry , organosilicon , hydrosilylation , acetal , silylation , brønsted–lowry acid–base theory , intramolecular force , silanes , catalysis , organocatalysis , aldehyde , organic chemistry , divergent synthesis , polymer chemistry , enantioselective synthesis , silane
Abstract A novel metal‐free intramolecular Brønsted‐acid‐catalyzed domino deprotection–hydrosilylation with hydrosilanes has been developed, and the unexpected Brønsted‐acid‐catalyzed intermolecular hydrolytic oxidation to functional siloxanes was described for the divergent and facile synthesis of functionalized siloxanes containing aldehyde motifs. We propose that these reactions proceed via neighboring acetal‐assisted Si–H bond activation. In addition, a related reaction is expected to open up further opportunities for the development and application of functional organosilicon compounds by organocatalysis.