Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.
A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized γ-amino acids in good yields with high regioselectivity.
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
John A
JA
Gurak
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Kin S
KS
Yang
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Zhen
Z
Liu
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Keary M
KM
Engle
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D000634:Aminoquinolines / Q000737:chemistry; D002087:Butyrates / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D009584:Nitrogen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D000588:Amines; D000596:Amino Acids; D000634:Aminoquinolines; D002087:Butyrates; D007202:Indicators and Reagents; D010165:Palladium; C479121:3-butenoic acid; D009584:Nitrogen