1421712-14-2Relevant academic research and scientific papers
Copper-catalyzed cross-coupling of boronic esters with aryl iodides and application to the carboboration of alkynes and allenes
Zhou, Yiqing,You, Wei,Smith, Kevin B.,Brown, M. Kevin
supporting information, p. 3475 - 3479 (2014/04/03)
Copper-catalyzed Suzuki-Miyaura-type cross-coupling and carboboration processes are reported. The cross-couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for orthogonal reactivity compared to palladium-catalyzed processes. The carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic esters. The alkyne carboboration method is highlighted in the simple one-pot synthesis of Tamoxifen. Cross-Cu-pling: The title cross-couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for reactivity orthogonal to that of the palladium-catalyzed processes. The title carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic esters. The alkyne carboboration method is highlighted in a simple one-pot synthesis of Tamoxifen.
Copper-catalyzed three-component borylstannylation of alkynes
Takemoto, Yuki,Yoshida, Hiroto,Takaki, Ken
, p. 14841 - 14844 (2013/01/15)
Regio- and stereoselective installation of boryl and stannyl moieties into a carbon-carbon triple bond of various alkynes has been achieved based on a three-component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate-tricyclohexylphosphine complex, giving diverse vic-borylstannylalkenes in a straightforward manner. Carbon-tin and carbon-boron bonds of the resulting borylstannylation product are successively transformed into carbon-carbon bonds by a Migita-Kosugi-Stille and a Suzuki-Miyaura coupling, leading to the formation of (Z)-tamoxifen with anti-breast cancer activity. Borylstannylation: A copper-tricyclohexylphosphine complex was found to catalyse the three-component borylstannylation of alkynes with a diboron and a tin alkoxide to afford vic-borylstannylalkenes in a regio- and stereoselective manner. Synthetic utility of the resulting borylstannylation product was demonstrated by a three-step synthesis of (Z)-tamoxifen from commercially available substrates by successive Migita-Kosugi-Stille and Suzuki-Miyaura couplings (see scheme). Copyright
