4 years ago

Ligand-Enabled γ-C(sp3)–H Cross-Coupling of Nosyl-Protected Amines with Aryl- and Alkylboron Reagents

Ligand-Enabled γ-C(sp3)–H Cross-Coupling of Nosyl-Protected Amines with Aryl- and Alkylboron Reagents
Qing-Feng Wu, Qian Shao, Jin-Quan Yu, Jian He
Pd(II)-catalyzed γ-C(sp3)–H cross-coupling of 4-nitrobenzenesulfonyl (Ns)-protected amines is realized using both arylboron and alkylboron coupling partners. An acetyl-protected aminomethyl oxazoline (APAO) ligand is found to enable the C(sp3)–H arylation reaction, whereas mono-N-protected amino acid (MPAA) ligands promote the C(sp3)–H cross-coupling with various alkylboron reagents. Notably, the APAO-promoted C–H arylation reactions afford high diastereoselectivity (>20:1), providing a useful method for modifying chiral amines. The use of a common nosyl protecting group to direct C(sp3)–H activation significantly improves the practicality of this transformation, as demonstrated by the gram-scale stereoselective synthesis of γ-aryl- and γ-alkyl-α-amino acids.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02721

DOI: 10.1021/acscatal.7b02721

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