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Highly Efficient Syntheses of Azetidines, Pyrrolidines, and Indolines via Palladium Catalyzed Intramolecular Amination of C(sp3)-H and C(sp2)-H Bonds at γ and δ Positions

Gang He, Yingsheng Zhao, Shuyu Zhang, Chengxi Lu and Gong Chen*

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States, Email: Guc11psu.edu

G. He, Y. Zhao, S. Zhang, C. Lu, G. Chen, J. Am. Chem. Soc., 2012, 134, 3-6.

DOI: 10.1021/ja210660g (free Supporting Information)


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Abstract

Palladium-catalyzed intramolecular amination of unactivated C-H bonds at the γ and δ positions of picolinamide (PA) protected amine substrates enables the synthesis of azetidine, pyrrolidine, and indoline compounds. The method features relatively low catalyst loading, use of inexpensive reagents, convenient operating conditions and predictable selectivities.

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Key Words

azetidines, pyrrolidines, iodosobenzene diacetate


ID: J48-Y2012-0000