Categories: C-B Bond Formation > Synthesis of potassium trifluoroborates >
Synthesis of allyltrifluoroborates
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Recent Literature
Allyl alcohols were regio- and stereoselectively converted to allyl boronic
acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron
with high isolated yields using palladium pincer-complex catalysis. A
mechanism for the fast allylic displacement of a hydroxy group is discussed.
V. J. Olsson, S. Sebelius, N. Selander, K. J. Szabó, J. Am. Chem. Soc.,
2006,
128, 4588-4589.
A mild, selective, palladium-catalyzed boronation of vinyl cyclopropane,
vinyl aziridine, and allyl acetate substrates could be accomplished using
tetrahydroxydiboron in the presence of a palladium pincer complex catalyst
to give synthetically useful linear trifluoro(allyl)borates or allyl
boronates incorporating a trans double bond. Functionalities such as
Br, COOEt, ArSO2(NH), OAc, and SiRMe2 are tolerated.
S. Sebelius, V. J. Olsson, K. J. Szabó, J. Am. Chem. Soc.,
2005,
127, 10478-10479.
S. Sebelius, V. J. Olsson, K. J. Szabó, J. Am. Chem. Soc.,
2005,
127, 10478-10479.
3-Substituted-2-alkoxycarbonyl allylboronates are readily produced by the
cross-coupling of Baylis-Hillman acetate adducts and bis(pinacolato)diboron in
the presence of a palladium catalyst. Subsequent addition of excess aqueous KHF2
gives stable allyl trifluoroborate salts. Allylboronate and allyltrifluoroborate
derivatives react stereoselectively with aldehydes to afford functionalized
homoallylic alcohols.
G. W. Kabalka B. Venkataiah, G. Dong, J. Org. Chem., 2004,
69, 5807-5809.
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