Catalytic dicyanative [4 + 2] cycloaddition triggered by cyanopalladation using ene-enynes and cyclic enynes with methyl acrylate

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7573-7579

  Arai, Shigeru ^a   Koike, Yuka ^a   Hada, Hirohiko ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; [4+2] CYCLOADDITION REACTIONS; A-THERMAL; CONJUGATED ENYNES; CYCLOADDUCTS; EXO-CYCLIZATION; IN-SITU; METHYL ACRYLATES; REGIO-SELECTIVE; STEREOGENIC CENTERS; STERIC BULK;

CYCLOADDITION; OLEFINS; PALLADIUM; REGIOSELECTIVITY; STEREOCHEMISTRY;

CYCLIZATION;

1,2 DICYANOALKENE DERIVATVE; ACRYLIC ACID METHYL ESTER; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ENYNE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CYANOPALLADATION; CYCLIZATION; CYCLOADDITION; STEREOCHEMISTRY; THERMAL ANALYSIS;

ACRYLATES; ALKYNES; CATALYSIS; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; NITRILES; PALLADIUM; STEREOISOMERISM;

EID: 78449238093     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100995k     Document Type: Article

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32. As the one of the reviewers indicates, another reaction pathway is also possible. If the alkenylpalladium species by initial cyanopalladation could be directly converted to cyclohexenylpalladium species via [4 + 2] cycloaddition, the following reductive elimination would give the same products, as shown below. Further investigation to evaluate this possibility is currently underway.