Electronic control of the regiochemistry in the Heck reaction

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3503-3508

  Von Schenck, Henrik ^a   Åkermark, Björn ^b   Svensson, Mats ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHELATION; CHEMICAL BONDS; ELECTRIC CHARGE; POSITIVE IONS; PROPYLENE; STEREOCHEMISTRY;

HECK REACTION;

ORGANOMETALLICS;

METAL COMPLEX; NITROGEN; OXYGEN; PALLADIUM COMPLEX; PHENYL GROUP; PHOSPHORUS; PROPYLENE;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; ENERGY; HECK REACTION; THERMODYNAMICS;

EID: 0037467444     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028755o     Document Type: Article

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31. 7-b and 8-b are kept out of the discussion at this point since the steric bulk of the t-Bu group influences the relative energies considerably. Steric influences will be discussed below.
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35. dppe = bis(diphenylphosphino)ethane, dppp = bis(diphenylphosphino)propane.
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38. The reaction barrier 7-b → 7-TS(2,1) is 22.0 kcal/mol and the reaction barrier 7-b → 8-TS(1,2) is 19.9 kcal/mol.
39. The π-complexation energy, ΔEπ, is 25.2 kcal/mol for 5-b and 18.8 kcal/ mol for 7-b.