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C-H to C-N Cross-Coupling of Sulfonamides with Olefins.

ABSTRACT: Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp³)-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 π-allyl Pd.

SUBMITTER: Ma R

PROVIDER: S-EPMC6415751 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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C-H to C-N Cross-Coupling of Sulfonamides with Olefins.

Ma Rulin R White M Christina MC

Journal of the American Chemical Society 20180221 9

Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp<sup>3</sup>)-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:bra ...[more]

PMID: 29432000

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