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Synthesis 2013; 45(5): 581-591
DOI: 10.1055/s-0032-1318218
DOI: 10.1055/s-0032-1318218
short review
Palladium-Catalyzed Synthesis of Carbo- and Heterocycles through Norbornene-Mediated ortho C–H Functionalization
Further Information
Publication History
Received: 16 December 2012
Accepted after revision: 24 January 2013
Publication Date:
07 February 2013 (online)
Abstract
Direct aromatic functionalization based on the use of a palladium catalyst and norbornene is a useful method to achieve straightforward synthesis of carbo- and heterocyclic compounds. New ring formation occurs through a cascade process triggered by ortho C–H alkylation (inter- and intramolecular) or arylation (homo- and heterocoupling) of aryl iodides. Up to four new carbon–carbon bonds are generated under palladium control in a single operation.
1 Introduction
2 ortho C–H Alkylation
2.1 Intermolecular ortho C–H Alkylation
2.1.1 Heck Reaction
2.1.2 C–N Coupling
2.1.3 C–H Arylation
2.2 Intramolecular ortho C–H Alkylation
2.2.1 Heck Reaction
2.2.2 Cyanation Coupling
2.3 Coupling Inter- and Intramolecular ortho C–H Alkylation
3 ortho C–H Arylation
3.1 Homocoupling
3.2 Heterocoupling
3.2.1 α-Arylation/CO Addition
3.2.2 Heck Reaction
3.2.3 C–N Coupling
4 Conclusion
-
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