Moon Sanghun, Nishii Yuji, Miura Masahiro
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Org Lett. 2021 Jan 1;23(1):49-53. doi: 10.1021/acs.orglett.0c03674. Epub 2020 Dec 11.
A rhodium-catalyzed oxidative annulation of benzimidates with elemental sulfur for the direct construction of isothiazole rings is reported. The proposed reaction mechanism involving Rh(I)/Rh(III) redox is supported by a stoichiometric reaction of metallacycle species as well as DFT calculations. This method is also applicable to selenium cyclization to produce isoselenazole derivatives. The alkoxy substituent at C3 can be used for further functionalization of the azole core.
报道了一种铑催化的苯并咪唑酯与元素硫的氧化环化反应，用于直接构建异噻唑环。涉及Rh(I)/Rh(III)氧化还原的反应机理通过金属环物种的化学计量反应以及密度泛函理论计算得到支持。该方法也适用于硒环化反应以制备异硒唑衍生物。C3位的烷氧基取代基可用于唑环核心的进一步官能化。
