Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300828
Keywords
Dichloromethylation; 1,2-Aryl migration; Allylic alcohols; Chlorocyclopropanes; Radical-addition
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A method for constructing γ,γ-dichloroketones through CHCl3-induced radical-dichloromethylation and 1,2-aryl migration was developed. The more electron-deficient aryl group in para-substituted unsymmetrical substrates was found to migrate preferentially. Moreover, chlorocyclopropanes could be obtained from allylic alcohols through radical-addition/1,2-aryl migration/nucleophilic substitution in a one-pot manner.
A radical-induced dichloromethylation and concomitant 1,2-aryl migration of allylic alcohols with CHCl3 is developed for the construction of gamma,gamma-dichloroketones in moderate to good yields. We found that, for the para-substituted unsymmetrical substrates, the more electron-deficient aryl group migrates preferentially over the more electron-rich aryl group. Moreover, chlorocyclopropanes could be obtained from allyl alcohols in one-pot manner through radical-addition/1,2-aryl migration/nucleophilic substitution.
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