Highly regiocontrolled pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6251-6256

  Rubin, Michael ^a   Markov, Jelena ^a   Chuprakov, Stepan ^a   Wink, Donald J ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING;

CATALYSIS; SYNTHESIS (CHEMICAL);

ISOMERS;

ALKYNE DERIVATIVE; ALLENE DERIVATIVE; ALLENYLPHOSPHINE OXIDE; PALLADIUM; PHOSPHINE OXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041529949     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034486o     Document Type: Article

References (37)

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26. TCPC = [1,2,3,4-tetrakis(methoxycarbonyl)-1,3-butadiene-1,4-diyl]palladium; TTMPP = tris(2,4,6-trimethoxyphenyl)phosphine.
27. 2i that Pd(0) complexes enable head-to-tail homo- and cross-coupling of acetylenes to be catalyzed.
28. Significant deuterium scrambling between deuterated terminal acetylenes and eventual proton sources in the presence of transition metals is well documented. See refs 2h and 3a,b.
29. 4 (5-10 mol %) in THF or toluene (1 M) at 100-120°C;
30. 3P (20 mol %) in THF or toluene (1 M) at 60-80°C;
31. 2-AlCl, 25 mol %). No formation of benzannulation products was detected under the listed conditions.
32. Pd-catalyzed enyne-diyne benzannulation is a regiospecific process. The regiochemistry of this reaction was established previously (see ref 6a). Nonetheless, the regiochemistry of the selected benzannulation product 5h was again confirmed by 2D NMR experiments; see Supporting Information for details.
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