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Synthesis of α‐Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis
Author(s) -
Fei Jun,
Wang Zhen,
Cai Zheren,
Sun Hao,
Cheng Xu
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500646
Subject(s) - hydroamination , chemistry , amine gas treating , catalysis , organic chemistry , tertiary amine , solubility , combinatorial chemistry
An efficient and mild trifluoromethanesulfonic acid‐catalyzed hydroamination of unfunctionalized alkenes to afford α‐tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2‐Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one‐pot, redox‐neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo‐ and regioselectivities by means of a cascade hydroamination reaction of β‐caryophyllene.