Studies on the heck reaction with alkenyl phosphates: Can the 1,2-migration be controlled? Scope and limitations

Journal of the American Chemical Society

Volumn 129, Issue 21, 2007, Pages 6931-6942

  Ebran, Jean Philippe ^a   Hansen, Anders L ^a   Gøgsig, Thomas M ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; CATALYTIC SYSTEMS; COUPLING REACTIONS; DIENE PRODUCTS;

CARBON; CATALYSTS; OLEFINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

PHOSPHATES;

ALKENYL GROUP; CARBON; HALIDE; LIGAND; LITHIUM CHLORIDE; OXYGEN; PALLADIUM; PALLADIUM CHLORIDE; PHOSPHATE; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; HECK REACTION; ISOMERIZATION; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALKENES; MESYLATES; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM; VINYL COMPOUNDS;

EID: 34249796975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070321b     Document Type: Article

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182. (a) Camp, D.; Matthews, C. F.; Neville, S. T.; Rounes, M.; Scott, R. W.; Truong, Y. Org. Process Res. Dev. 2006, 10, 814.
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184. 2 and X-phos as the catalytic system (see ref 36a).
185. Possibly the alkenyl phosphates bearing a Cl-quaternary carbon possess longer and hence weaker Cl-O bonds due to unfavorable sterical interactions between the phosphate group and the Cl-substituent compared to Cl-alkyl substituents with an α-proton, which facilitates their entry into the first step of the catalytic cycle.
186. A simple base induced elimination reaction of the vinyl tosylate involving the α-proton of the alkyl side chain would lead to the formation of a volatile trisubstituted allene. Alternatively, if the oxidative addition step is more facile with vinyl tosylates than with the phosphates, the generated alkenyl-Pd(II) intermediate could undergo a β-hydride elimination step again involving the same alkyl sidechain with the formation of an allene, which competes successfully with either the insertion step or the elimination of the olefin hydrogen.
187. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.