Mg-Promoted Regioselective Cross-Coupling of Stilbene Derivatives with Carbonyl Compounds

Synlett

Volumn , Issue 1, 2004, Pages 30-36

  Yamamoto, Yoshimasa ^a   Kawano, Seiji ^a   Maekawa, Hirofumi ^a   Nishiguchi, Ikuzo ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Cross coupling; Electron transfer; Magnesium; Reductions; Regioselectivity

Indexed keywords

BENZYL DERIVATIVE; CARBONYL DERIVATIVE; CHLOROTRIMETHYLSILANE; ION; MAGNESIUM; N,N DIMETHYLFORMAMIDE; PHENETHYL ALCOHOL; STILBENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; STEREOCHEMISTRY;

EID: 0346334406     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44970     Document Type: Article

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34. The use of less than 10 equiv mol of acetone(2a) resulted in decrease in the yield of phenethyl alcohols 3a accompanying increase in formation of tarry material. Thus, the use of 3 equiv mol and 5 equiv mol of 2a provided 3a in 58% and 63% yields, respectively.
35. General Methods: Stilbene 1a, acenaphthylene (7a), aliphatic carbonyl compounds 2, TMSC1, Mg and levulinic acid esters were purchased from Aldrich Chemical Co. Ltd, Tokyo Kasei Kogyo Co. Ltd or Nacalai Tesque Ltd, and were used without further purification.
36. +].
37. +].
38. The possibility of protonation prior to the electrophilic attack of carbonyl compounds 2 on the anion radical species 9 may be excluded in the present cross-coupling because the first protonation to 9 generated from α-methylstilbene(1a) lead to generation of more unstable tertiary carbanion, which may be difficult to form, in order to confirm the observed regioselectivity.
39. As another possible explanation for unusual regioselectivity of this reaction, it may seem operative that the tertiary carbanion of the α-position of the anion radical species 9 may be more unstable, but more reactive than the secondary carbanion of 9 to be preferentially subjected to electrophilic attack of carbonyl compounds 2.
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