Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media.
Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to afford 1,8-diaminonaphthalene protected (Z)-β-boryl enoates and primary, secondary, and tertiary enamides in good to excellent yields. These reactions demonstrate a high tolerance toward a variety of alkyl, aryl, and heteroatom functional groups and provide convenient access to a diverse range of vinylboronic acid derivatives.
Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Amanda K
AK
Nelson
Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Cheryl L
CL
Peck
Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Sean M
SM
Rafferty
Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Webster L
WL
Santos