Using a simple copper(I) catalyst has allowed a high yielding sulfonylative-Suzuki–Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate
Conjugate-addition of phenyldimethylsilyllilthium (or cuprate) to vinyl sulfones followed by in situ alkylation of the alpha-sulfonyl anion provides alpha-alkylated beta-silyl sulfones. Treatment of these materials with fluoride provides trisubstituted olefins via the Kocienski olefin synthesis.
Conversion of Cyclic Vinyl Sulfones to Transposed Vinyl Phosphonates
作者:Mohammad N. Noshi、Ahmad El-awa、Eduardo Torres、Philip L. Fuchs
DOI:10.1021/ja072890p
日期:2007.9.1
Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.