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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 (free Supporting Information)


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.

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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.


Key Words

Allylic Alcohols, 1,3-Dienes, Hydrogen Peroxide


ID: J54-Y2010-2740