Et3B-promoted, Pd(0)-catalyzed allylation of active methylene compounds with allylic alcohols

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5705-5709

  Tamaru, Yoshinao ^a   Horino, Yoshikazu ^a   Araki, Misato ^a   Tanaka, Shuji ^a   Kimura, Masanari ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Alcohols; Allylation; Boron and compounds; Palladium and compounds

Indexed keywords

ALLYL ALCOHOL; BORANE DERIVATIVE; CARBENE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0034702561     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00934-5     Document Type: Article

References (20)

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17. 4) and the solvent was removed in vacuo. Purification of the residue by column chromatography over silica gel (hexane-ethyl acetate 32/1, v/v) provided 3a: 209.0 mg (80% yield).
18. Stary, I.; Stara, I. G.; Kocovsky, P. Tetrahedron Lett. 1993, 34, 179.
19. 3B is able to promote both the Pd(0)-catalyzed nucleophilic and electrophilic allylations starting from allylic alcohols. The complex I has also been proposed as an intermediate for the former process, where it undergoes allyl-ethyl exchange to generate allyl(diethyl)borane and EtPd(II)(OH).
20. 3B in a stoichiometric amount in order to obtain the better yields and to promote the reaction at a reasonable rate.