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The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive Functionalization
Author(s) -
Schlosser Manfred
Publication year - 2005
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.200300645
Subject(s) - electrophile , toolbox , reactivity (psychology) , combinatorial chemistry , group 2 organometallic chemistry , surface modification , chemistry , halogen , computer science , nanotechnology , biochemical engineering , organic chemistry , materials science , molecule , catalysis , engineering , programming language , medicine , alkyl , alternative medicine , pathology
This Review describes a concept aimed at rational and maximal structure proliferation. To this end, simple aromatic or heterocyclic starting materials, often bulk chemicals, are converted into all regionisomerically possible polar organometallic intermediates (mostly lithiated species), which then may be combined with any of the countless electrophiles to provide attractive new building blocks, particularly functionalized derivatives. The practical implementation relies on a set (“toolbox”) of sophisticated recipes developed by mechanistically guided modification of the two most prominent exchange methods used for the generation of polar organometallic compounds: hydrogen–metal and halogen–metal interconversion. These mutant methods (“old methods in a new outfit”) amplify the existing options for organic synthesis by ensuring maximum regioflexibility. At the same time they offer new insight into factors that govern organometallic reactivity and provide hints on how to alter or finetune this reactivity judiciously.