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Ligand-Controlled Regioselective Pd-Catalyzed Diamination of Alkenes

Xiaojian Liu, Chuanqi Hou, Yiyuan Peng*, Pinhong Chen* and Guosheng Liu*

*Jiangxi Normal University, Nanchang 330022; Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China, Email: yypengjxnu.edu.cn, pinhongchenmail.sioc.ac.cn, gliumail.sioc.ac.cn

X. Liu, C. Hou, Y. Peng, P. Chen, G. Liu, Org. Lett., 2020, 22, 9371-9375.

DOI: 10.1021/acs.orglett.0c03634 (free Supporting Information)


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Abstract

Depending on the steric hindrance of the ligand, a regioselective palladium-catalyzed diamination of unactivated alkenes, provides either amino-functionalized piperidines or pyrrolidines. 6-Endo diamination occurred with a less sterically hindered quinox ligand to afford 3-aminopiperidines, while 5-exo diamination occurred with a bulky pyox ligand to give amino-substituted pyrrolidines.

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Key Words

piperidines, pyrrolidines, NFSI


ID: J54-Y2020