Abstract
This literature review focuses on the use of metal- or metalloid-based reagents to
generate ortho- arynes from stable precursors via organometallic intermediates or to generate organometallic
complexes of ortho- arynes. The review also encompasses the capture of arynes by organometallics to generate
new complexes, with interesting reactivity in their own right, or as intermediates
in catalytic systems. The purpose of the review is to highlight the novelty, utility
and versatility of the interaction of organometallic species with arynes and their
precursors. These points are illustrated through a number of examples of the application
of such methods in the preparation of complex organic molecules. The review contains
some 197 references and covers the literature up to May 2006.
1 Introduction
2 Organometallic Generation of Arynes
2.1 Background and History
2.2 Orthometallation and Deprotonation
2.3 Halogen-Metal Exchange
2.4 Carbon-Silicon Cleavage
2.5 Miscellaneous Routes
3 Organometallic Capture or Complexation of Arynes
3.1 General Modes of Addition or Complexation of Organometallics to Arynes
3.2 Non-Aryne-Capture Routes to Organometallic Aryne Complexes
3.3 Gas-Phase Chemistry of Organometallic Aryne Complexes
3.4 Stoichiometric Organometallic Addition to Arynes
3.5 Catalytic Capture and Transformations of Arynes
4 Summary and Outlook
Key words
arynes - organometallic reagents - catalysis - main group metals - transition metals
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