Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 9, Pages 3202-3205Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b13492
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Funding
- NIGMS MIRA [R35 GM122525]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM122525] Funding Source: NIH RePORTER
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Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp(3))-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear: -branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic pi-allyl Pd.
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