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Synthesis of propargylic sulfones

Recent Literature

A catalyst-free, environmentally benign protocol provides propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct via an in situ dehydrative cross-coupling process.
Y. Liu, P. Xie, Z. Sun, X. Wo, C. Gao, W. Fu, T.-P. Loh, Org. Lett., 2018, 20, 5353-5356.

The combination of Ph3P/ICH2CH2I promotes a dehydroxylative sulfonylation of benzylic and allylic alcohols with a variety of sulfinates in short reaction time. Using Ph2PMe and elevated temperatures, the protocol can be extended to alkyl alcohols. Various sulfonyl groups can be incorporated, such as CF3SO2 and HCF2SO2, which are fluorinated groups of interest in pharmaceutical chemistry.
Y.-J. Xiang, S.-Liu, J. Zhou, J.-H. Lin, X. Yao, J.-C. Xiao, J. Org. Chem., 2023, 88, 4818-4828.

In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields. A catalysis with byproduct HCl is involved in this new protocol.
H.-H. Li, D.-J. Dong, Y.-H. Jin, S.-K. Tian, J. Org. Chem., 2009, 74, 9501-9504.