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Copper‐catalyzed C‐H Bis‐nitration of 1‐Naphthylamide Derivatives with tert‐Butyl Nitrite as Nitro Source
Author(s) -
Li Jizhen,
Qin Zengxin,
Zhang Changjing,
Zhang Yingchao,
Wen Chunxia
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901177
Subject(s) - nitration , nitrite , chemistry , catalysis , nitro , medicinal chemistry , copper , combinatorial chemistry , organic chemistry , nitrate , alkyl
A simple and atom‐economical protocol for bis‐nitration of 1‐naphthylamides was firstly discovered with tert ‐butyl nitrite (TBN) as nitro source and catalyzed by Cu(OAc) 2 . Assisted by picolinamide direction, the C2,4‐H bis‐nitration could be achieved with excess amount of TBN at 50°C in HOAc. A radical pathway and single electron transfer process might be involved in the bis‐nitration process.