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Lewis Base Catalysis in Organic Synthesis
Author(s) -
Denmark Scott E.,
Beutner Gregory L.
Publication year - 2008
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.200604943
Subject(s) - lewis acids and bases , frustrated lewis pair , chemistry , hydrogen bond catalysis , electrophile , nucleophile , catalysis , reactivity (psychology) , combinatorial chemistry , organic chemistry , enantioselective synthesis , organocatalysis , medicine , alternative medicine , pathology
The legacy of Gilbert Newton Lewis (1875–1946) pervades the lexicon of chemical bonding and reactivity. The power of his concept of donor–acceptor bonding is evident in the eponymous foundations of electron‐pair acceptors (Lewis acids) and donors (Lewis bases). Lewis recognized that acids are not restricted to those substances that contain hydrogen (Brønsted acids), and helped overthrow the “modern cult of the proton”. His discovery ushered in the use of Lewis acids as reagents and catalysts for organic reactions. However, in recent years, the recognition that Lewis bases can also serve in this capacity has grown enormously. Most importantly, it has become increasingly apparent that the behavior of Lewis bases as agents for promoting chemical reactions is not merely as an electronic complement of the cognate Lewis acids: in fact Lewis bases are capable of enhancing both the electrophilic and nucleophilic character of molecules to which they are bound. This diversity of behavior leads to a remarkable versatility for the catalysis of reactions by Lewis bases.