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Silicon‐Based Cross‐Coupling Reactions in the Total Synthesis of Natural Products
Author(s) -
Denmark Scott E.,
Liu Jack H.C.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200905657
Subject(s) - organosilicon , bifunctional , silicon , coupling reaction , substrate (aquarium) , silylation , moiety , reagent , coupling (piping) , total synthesis , natural product , chemistry , combinatorial chemistry , carbon fibers , catalysis , nanotechnology , materials science , organic chemistry , metallurgy , oceanography , composite number , composite material , geology
Unlike other variants of transition‐metal‐catalyzed cross‐coupling reactions, those based on organosilicon donors have not been used extensively in natural product synthesis. However, recent advances such as: 1) the development of mild reaction conditions, 2) the expansion of substrate scope, 3) the development of methods to stereoselectively and efficiently introduce the silicon‐containing moiety, 4) the development of a large number of sequential processes, and 5) the advent of bifunctional bis(silyl) linchpin reagents, signify the coming of age of silicon‐based cross‐coupling reactions. The following case studies illustrate how silicon‐based cross‐coupling reactions play a strategic role in constructing carbon–carbon bonds in selected target molecules.