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Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones
Author(s) -
Zhao Zhensheng,
Kulkarni Kaivalya G.,
Murphy Graham K.
Publication year - 2017
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.201700393
Subject(s) - chemistry , hypervalent molecule , hydrazone , halogen , benzaldehyde , reagent , iodine , diazo , fluorine , organic chemistry , tandem , chlorine , combinatorial chemistry , catalysis , alkyl , materials science , composite material
We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl 2 and TolIF 2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non‐α‐stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF 2 ) and aryldichloromethane (ArCHCl 2 ) derivatives.