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Regiospecific Synthesis of Substituted 2‐Nitrobenzaldehydes from Benzaldehydes through Palladium‐Catalyzed Chelation‐Assisted C–H Nitration
Author(s) -
Zhang Wei,
Wu Degui,
Zhang Jian,
Liu Yunkui
Publication year - 2014
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.201402451
Subject(s) - nitration , chemistry , palladium , catalysis , chelation , combinatorial chemistry , organic chemistry , medicinal chemistry
Abstract A regiospecific synthesis of substituted 2‐nitrobenzaldehydes from substituted benzaldehydes has been developed that involves a three‐step process with palladium‐catalyzed chelation‐assisted C–H nitration as the key step. In the process, O ‐methyl aldoxime serves as a removable directing group for the palladium‐catalyzed ortho ‐nitration of substituted benzaldoximes and it can be removed in subsequent conversion of the resulting 2‐nitrobenzaldoximes into 2‐nitrobenzaldehydes.