Given the ubiquity of C—N bonds in natural products and pharmaceuticals, the cross-coupling of nitrogen functionality with hydrocarbons under fragment coupling conditions (1 equivalent) stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)—N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) 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. &gt;20:1 linear:branched, &gt;20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization likely by supporting cationic π-allyl Pd.

C–H to C–N cross-coupling of sulfonamides with olefins

256th National Meeting (2018)

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