Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides
Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N -formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.
Huy, Peter Helmut
supporting information
p. 2474 - 2483
(2019/06/08)
Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones
We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 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 (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).
Zhao, Zhensheng,Kulkarni, Kaivalya G.,Murphy, Graham K.
supporting information
p. 2222 - 2228
(2017/07/07)
A simple and efficient procedure for the preparation of benzal chlorides and benzal bromides
Benzal chlorides and benzal bromides were conveniently synthesized by reaction of aryl aldehydes with a Vilsmeier type reagent formed in situ by reduction of CCl4 or CBr4 in dimethylformamide (DMF) as solvent.
AN EFFECTIVE CHLORINATING AGENT BENZYLTRIMETHYLAMMONIUM TETRACHLOROIODATE, BENZYLIC CHLORINATION OF ALKYLAROMATIC COMPOUNDS
The reaction of alkylaromatic compounds with benzyltrimethylammonium tetrachloroiodate in carbon tetrachloride in the presence of AIBN under reflux for several hours gave α-chloro-substituted compounds in fairly good yields.