Ni(0)-Catalyzed 1,4-Selective Diboration of Conjugated Dienes

Robert J. Ely and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: morkenbc.edu

R. J. Ely, J. P. Morken, Org. Lett., 2010, 12, 4348-4351.

DOI: 10.1021/ol101797f

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Abstract

A catalytic stereoselective 1,4-diboration of conjugated dienes with B₂(pin)₂ and the presence of Ni(cod)₂ and PCy₃ as the catalyst roceeds efficiently at low catalyst loadings and broadens the substrate scope of current methods for catalytic diene diboration by including internal and sterically hindered. The intermediate allylboronate was oxidized to the stereodefined allylic 1,4-diol.

see article for more examples

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Catalytic Enantioselective Diboration of Cyclic Dienes. A Modified Ligand with General Utility

K. Hong, J. P. Morken, J. Org. Chem., 2011, 76, 9102-9108.

Regio- and Stereoselective Ni-Catalyzed 1,4-Hydroboration of 1,3-Dienes: Access to Stereodefined (Z)-Allylboron Reagents and Derived Allylic Alcohols

R. J. Ely, J. P. Morken, J. Am. Chem. Soc., 2010, 132, 2534-2535.

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Key Words

Allylic Alcohols, 1,3-Dienes, Hydrogen Peroxide

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ID: J54-Y2010-2740