On the Configurational Stability of Chiral Heteroatom-Substituted [D₁]Methylpalladium Complexes as Intermediates of Stille and Suzuki-Miyaura Cross-Coupling Reactions.

ABSTRACT: Enantiomerically pure (S)-tributylstannyl[D₁]methanol and (R)- and (S)-tributylstannyl[D₁]methyl benzoates were Stille-coupled with bromobenzene and benzoyl chloride in 1,4-dioxane and toluene using [(Ph₃P)₄Pd] or [(Ph₃P)₂PdCl₂] either alone or in combination with CuCN as cocatalyst at temperatures up to 80 °C. The products were found to be enantiomerically pure. (R)- and (S)-N-(tributylstannyl[D₁]methyl)phthalimides gave enantiomerically pure products with benzoyl chloride, but with bromobenzene protected phenyl[D₁]methylamines gave products of only 52-69 % ee depending on the solvent used. Tributyl(thio[D₁]methyl)stannanes could no

SUBMITTER: Malova Krizkova P 

PROVIDER: S-EPMC3790956 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature