Brønsted base-modulated regioselective pd-catalyzed intramolecular aerobic oxidative amination of alkenes: formation of seven-membered amides and evidence for allylic C-H activation.
A novel palladium-catalyzed intramolecular aerobic oxidative allylic C-H amination of olefins has been developed. Brønsted base can modulate the regioselectivity, favoring the formation of 7-membered rings. Mechanistic studies using deuterium-labeled substrates as probes support a rate-determining allylic C-H activation/irreversible reductive elimination pathway.
Wu
Liang
L
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China, 200032.
Qiu
Shuifa
S
Liu
Guosheng
G
D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000577:Amides; D010165:Palladium