Categories: C-B Bond Formation > Synthesis of boronic acids and boronates >
Synthesis of alkylboronic acids and alkylboronates
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Hydroboration of terminal and internal aliphatic alkenes with
pinacolborane was carried out at room temperature in the presence of dppm and [Ir(cod)Cl]2 resulting in addition of the boron atom to the terminal carbon with a selectivity of more than
99%. A complex
prepared from dppe and [Ir(cod)Cl]2 resulted in the best yields for
vinylarenes.
Y. Yamamoto, R. Fujikawa, T. Umemoto, N. Miyaura, Tetrahedron,
2004,
60, 10695-10700.
Rhodium-catalyzed asymmetric hydroboration of 3,3-disubstituted cyclopropenes
gave 2,2-disubstituted cyclopropyl boronates with high degrees of diastereo- and
enantioselectivity. Suzuki cross-coupling reaction of selected
cyclopropylboronic derivatives produced corresponding optically active aryl- and
vinylcyclopropanes in good yields.
M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc., 2003,
125, 7198-7199.
A dramatic rate acceleration in the copper-catalyzed addition of bis(pinacolato)diboron
to α,β-unsaturated carbonyl
compounds was realized by adding alcohol additives. Various α,β-unsaturated carbonyl compounds
were reacted to the corresponding β-boryl carbonyl compounds in high
yields.
R. Varala, S. Nuvula, S. R. Adapa, J. Org. Chem., 2006,
71, 8283-8286.
A nickel catalyst system enables the β-boration of di-, tri-, and
tetrasubstituted α,β-unsaturated esters and amides with bis(pinacolato)diboron
in good yields.
K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett., 2007,
9, 5031-5033.
