53312-88-2Relevant articles and documents
Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane
Liang, Yujie,Lin, Fengguirong,Adeli, Yeerlan,Jin, Rui,Jiao, Ning
supporting information, p. 4566 - 4570 (2019/02/14)
Although the application of 1,2-dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C?H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value-added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late-stage chlorination of bioactive molecules.
Formation of N-acetyl-2,3-dihydroindoles by the electrochemical cleavage of the carbon-chlorine bond in N-allyl-2-chloroacetanilides
Dias, Marylene,Gibson, Mandy,Grimshaw, James,Hill, Ian,Trocha-Grimshaw, Jadwiga,Hammerich, Ole
, p. 549 - 554 (2007/10/03)
The electrochemically induced radical cyclization of N-allyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-allyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-2,3-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained. Acta Chemica Scandinavica 1998.