Ligand-free heck reaction: Pd(OAc)2 as an active catalyst revisited

Journal of Organic Chemistry

Volumn 68, Issue 19, 2003, Pages 7528-7531

  Yao, Qingwei ^a   Kinney, Elizabeth P ^a   Yang, Zhi ^a,b  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

^b Shanxi Hydroelec Design Inst   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; ORGANIC SOLVENTS;

HECK REACTIONS;

PALLADIUM COMPOUNDS;

BASE; BROMIDE; LIGAND; N,N DIMETHYLACETAMIDE; PALLADIUM; PALLADIUM ACETATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; REACTION ANALYSIS; SOLVENT EFFECT;

EID: 0141566392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034646w     Document Type: Article

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63. Although we could not rule out the possibility of the involvement of a Pd(0) species in the catalytic cycle, the formation of palladium black, which could otherwise be expected at the reaction temperature and in the absence of a stabilizing ligand, was not observed throughout the reaction except when the acrylate was used as the terminal olefin.
64. By analogy to other palladacycles, I may exist in equilibration with its dimeric form: (diagram presented)
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66. Although the reactions reported in Tables 1-3 were run on 0.5-2 mmol scales, this protocol is readily scalable as exemplified by the following reactions perfomed on a 10 mmol scale: (diagram presented)