Direct C-H/C-X Coupling Methodologies Mediated by Pd/Cu or Cu: An Examination of the Synthetic Applications and Mechanistic Findings

TY - JOUR

T1 - Direct C-H/C-X Coupling Methodologies Mediated by Pd/Cu or Cu: An Examination of the Synthetic Applications and Mechanistic Findings

AU - De Ornellas, Sara

AU - Storr, Thomas E.

AU - Williams, Thomas J.

AU - Baumann, Christoph G.

AU - Fairlamb, Ian J. S.

PY - 2011/2

Y1 - 2011/2

N2 - Organocopper chemistry has long been known to be powerful synthetic methodology leading to the generation of C-C, C-O, C-N, C-S and C-X bonds. Advances in catalytic and stoichiometric organometallic reactions for the formation of C-C bonds from unfunctionalised arenes, e. g. by activation-functionalisation of a C-H bond, provides diverse and applicable reaction conditions for direct functionalisation.This review covers the background, applications and recent advances made in the area of aromatic C-X/C-H-bond couplings promoted by copper and copper/palladium mixed systems. The efficacy and scope of these reactions are discussed and the different methodologies are placed into context. Mechanistic considerations and evidence are highlighted at appropriate junctures in the review.

AB - Organocopper chemistry has long been known to be powerful synthetic methodology leading to the generation of C-C, C-O, C-N, C-S and C-X bonds. Advances in catalytic and stoichiometric organometallic reactions for the formation of C-C bonds from unfunctionalised arenes, e. g. by activation-functionalisation of a C-H bond, provides diverse and applicable reaction conditions for direct functionalisation.This review covers the background, applications and recent advances made in the area of aromatic C-X/C-H-bond couplings promoted by copper and copper/palladium mixed systems. The efficacy and scope of these reactions are discussed and the different methodologies are placed into context. Mechanistic considerations and evidence are highlighted at appropriate junctures in the review.

KW - Copper

KW - C-H Functionalisation

KW - Palladium

KW - Nucleosides and Imidazoles

KW - CATALYZED DIRECT ARYLATION

KW - INCLUDING FREE (NH)-IMIDAZOLE

KW - DIRECT C-2 ARYLATION

KW - ARYL BOND FORMATION

KW - H ARYLATION

KW - 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES

KW - REGIOSELECTIVE SYNTHESIS

KW - LIGANDLESS CONDITIONS

KW - DIRECT ALKYNYLATION

KW - PURINE NUCLEOSIDES

UR - http://www.scopus.com/inward/record.url?scp=79551671096&partnerID=8YFLogxK

M3 - Article

SN - 1570-1794

VL - 8

SP - 79

EP - 101

JO - CURRENT ORGANIC SYNTHESIS

JF - CURRENT ORGANIC SYNTHESIS

IS - 1

ER -