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A Metal‐Free Oxidative Cross‐Dehydrogenative Coupling of N ‐Aryl Tetrahydroisoquinolines and 2‐Methylazaarenes Using a Recyclable Oxoammonium Salt as Oxidant in Aqueous Media
Author(s) -
Fang Li,
Li Zhenhua,
Jiang Zhijiang,
Tan Zhiyong,
Xie Yuanyuan
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600423
Subject(s) - chemistry , iminium , salt (chemistry) , tetrafluoroborate , oxidative phosphorylation , aqueous medium , nucleophile , aryl , oxidative coupling of methane , metal , aqueous solution , condensation , medicinal chemistry , organic chemistry , combinatorial chemistry , polymer chemistry , ion , ionic liquid , catalysis , biochemistry , alkyl , physics , thermodynamics
A metal‐free oxidative cross‐dehydrogenative coupling of N ‐aryl tetrahydroisoquinolines and 2‐methylazaarenes in water under mild conditions has been developed. 4‐Acetylamino‐2,2,6,6‐tetramethylpiperidine‐1‐oxoammonium tetrafluoroborate was employed as a mild oxidant that can be recovered and reused directly. The reaction proceeds through formation of an iminium ion in situ followed by condensation with various nucleophiles, providing the desired products in moderate to good yields.