Redox divergence strategy for the construction of (dihydro) thiophene with dimethyl sulfoxide

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(Dihydro) Thiophene is widely found in many natural products, functional materials, and biologically active compounds among the most common 5-membered heterocycles.

Sulfide sources are commonly used to prepare thiophene compounds through the formation of two new C–S bonds.However substrate The adoption of highly functionalized precursors limits range and functional group compatibility.

Recently, a research team led by Professor Chen Qing’an of the Dalian Institute of Chemical Physics (DICP) at the Chinese Academy of Sciences has developed a redox divergent structure for (dihydro) thiophene. Dimethyl sulfoxide (DMSO) As both an oxidizer and a sulfur donor.

This study was published in Angewandte Chemie International Edition August 30th.

Researchers used allyl alcohol, which is readily available as a starting material, and DMSO as a mild oxidant to efficiently provide derivatives of (dihydro) thiophene. They found that selective manipulation could be dominated by doses of DMSO and HBr.

In addition, they demonstrated that this redox divergent strategy can achieve programmable and concise synthesis of tetraarylthiophene, bioactive DuP 697, and its positional isomers. It may serve as a general platform for achieving five-numbered sulfur-containing heterocycles that are synthetically and medically useful.

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For more information:
Redox divergent construction of (dihydro) thiophene by Heng Liu et al, DMSO, Angewandte Chemie International Edition (2021). DOI: 10.1002 / anie.202109026

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