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2005
C-C bond formation
O 0282
A Highly Effective (Triphenyl phosphite)palladium Catalyst for a
Reaction of Allylic Alcohols with Organoboronic Acids. — The
13- 050 Cross—Coupling
cross-coupling reaction of the allylic alcohols (I) or (IV) with aryl boronic acids proceeds smoothly in toluene or dioxane in the presence of a (triphenylphosphite)palladium catalyst. Neither cocatalysts for promoting C—O bond cleavage of allylic alcohols
nor bases for activation of organoboron reagents are necessary, but electron-withdrawing phenyl substituents require higher amounts of the catalyst and a higher temperature.
The reaction tolerates F, Cl and Br, while 4-iodophenylboronic acid gives no
reaction. The observed rearrangement of crotyl alcohol (VII) may be derived from a
η3-allylpalladium intermediate. The cross coupling proceeds with inversion of configuration, as confirmed by the reaction of the cis-alcohol (X) at low conversion. —
(KAYAKI, Y.; KODA, T.; IKARIYA*, T.; Eur. J. Org. Chem. 2004, 24, 4989-4993;
Grad. Sch. Sci. Eng., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan; Eng.) —
Kieslich
2005
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