Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: regioselective and switchable C-H alkenylation and annulation of pyrroles.
A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.
Department of Chemistry, University of Cambridge, UK.
Elizabeth M
EM
Beck
Neil P
NP
Grimster
Richard
R
Hatley
Matthew J
MJ
Gaunt
D000332:Aerobiosis; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002413:Cations, Divalent; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D002413:Cations, Divalent; D011758:Pyrroles; D010165:Palladium