Article

BF3.Et2O-catalyzed direct carbon-carbon bond formation of alpha-EWG Ketene-(S,S)-acetals and alcohols and synthesis of unsymmetrical biaryls.

Department of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun 130024, P R China.
The Journal of Organic Chemistry (impact factor: 4.45). 02/2007; 72(1):139-43. DOI:10.1021/jo061775e pp.139-43
Source: PubMed

ABSTRACT A highly efficient BF3.OEt2-catalyzed formal dehydration C-C coupling reaction between readily available alpha-EWG ketene-(S,S)-acetals and various alcohols via direct substitution of the hydroxy group in alcohols has been developed. On the basis of this C-C coupling reaction, a series of alkylated alpha-EWG ketene-(S,S)-acetals and functionalized 1,4-pentanedienes were prepared in high to excellent yields and the unsymmetrical biaryls were synthesized in good yields from the generated 1,4-pentanedienes and nitroalkanes through a one-pot annulation-aromatization process.

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Keywords

C-C coupling reaction
 
direct substitution
 
efficient BF3.OEt2-catalyzed formal dehydration C-C coupling reaction
 
generated 1,4-pentanedienes
 
one-pot annulation-aromatization process
 
unsymmetrical biaryls
 

Qian Zhang