Open AccessPalladium-Catalyzed Allylic C−OH Functionalization for Efficient Synthesis of Functionalized Allylsilanes
Author(s) -
Nicklas Selander,
Jennifer R. Paasch,
Kálmán J. Szabó
Publication year - 2010
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja1096732
Subject(s) - chemistry , allylic rearrangement , reagent , palladium , silylation , catalysis , surface modification , combinatorial chemistry , organic chemistry , organic synthesis , natural product
A new method is described for palladium-catalyzed allylic silylation using allylic alcohols and disilanes as precursors. The reactions proceed smoothly under mild and neutral conditions, and this method is suitable for synthesis of regio- and stereodefined allylsilanes. The presented silylation reaction can be easily extended to include synthesis of allylboronates by change of the dimetallic reagent. The presented synthetic procedure offers a broad platform for the selective synthesis of functionalized allyl metal reagents, which are useful precursors in advanced organic chemistry and natural product synthesis.