Journal
ACS CATALYSIS
Volume 6, Issue 8, Pages 5295-5301Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01818
Keywords
palladium catalysis; allylic amidation; sp(3) C-H activation; N-heterocycles; terminal olefins
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Funding
- North Dakota State University
- NIH NIGMS [P30 GM103332]
- NSF CRIF [CHE-0946990]
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An atom-economic direct intermolecular allylic amidation of electron-deficient tautomerizable N-heterocycles is reported via allylic C-H activation of terminal olefins with a PdCl2 catalyst. The reaction did not require any activators (base or Lewis acid) or external ligands and proceeded with high chemo- (N vs O), regio- (linear vs branched), and stereoselectivity (E vs Z) for a variety of N-heterocycles and terminal olefins. Mechanistic investigation and stoichiometric studies validate the sulfoxide-ligand-assisted allylic C-H bond cleavage to form a pi-allylpalladium intermediate in the reaction pathway. Excellent selectivity was observed during intermolecular competition demonstrating the differential nucleophilicity of N-heterocycles and differential susceptibility of allyl C-H bond cleavage to form pi-allylpalladium complexes directly from terminal olefins.
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