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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.