Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones | Zendy

Zhao Zhensheng | Zendy; Kulkarni Kaivalya G. | Zendy; Murphy Graham K. | Zendy

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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.

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