Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 35, Pages 12194-12196Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja105096r
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- MEXT [20037031]
- JSPS
- Grants-in-Aid for Scientific Research [20037031] Funding Source: KAKEN
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The regioselectivity in the addition of silylboronic esters to terminal alkynes can be switched by the choice of phosphorus ligands on the palladium catalysts. The silaboration proceeds with normal regisoselectivity in the presence of (eta(3)-C(3)H(5))Pd(PPh(3))Cl (1.0 mol %) to give 1-boryl-2-silyl-1-alkenes in high yields. In sharp contrast, selective formation of the inverse regioisomers, 2-boryl-1-silyl-1-alkenes, takes place when the reaction is carried out with a palladium catalyst bearing P(t-Bu)(2)(biphenyl-2-yl). A reaction mechanism for the change of regioselectivity that involves reversible insertion/beta-boryl elimination steps is proposed.
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