State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology , Dalian University of Technology , Dalian , 116024 , P. R. China.
School of Chemical Engineering , Dalian University of Technology , Dalian , 116024 , P. R. China.
Org Lett. 2018 Nov 2;20(21):6705-6709. doi: 10.1021/acs.orglett.8b02794. Epub 2018 Oct 22.
A regiodivergent Rh(I)-catalyzed azide-alkyne cycloaddition (RhAAC) was developed for the synthesis of both fully substituted 4-sulfonyl-1,2,3-triazoles and 5-sulfonyl-1,2,3-triazoles in high regioselectivities and yields under mild conditions in one step. Nonmetallic sulfur(II) or sulfur(VI) could efficiently control the regioselectivity of RhAAC reactions by chelation or nonchelation mechanisms to give excellent 1,4- or 1,5-regioselectivities. The utility of this method is further highlighted by its compatibility with water and air, broad substrate scope, good functional group tolerance, gram-scale preparation, applicability to carbohydrates, and the tandem CuAAC-RhAAC reaction.
发展了一种区域发散的 Rh(I)催化的叠氮-炔环加成反应（RhAAC），用于在温和条件下一步高区域选择性和产率合成全取代的 4-磺酰基-1,2,3-三唑和 5-磺酰基-1,2,3-三唑。非金属硫（II）或硫（VI）可以通过螯合或非螯合机制有效地控制 RhAAC 反应的区域选择性，从而得到优异的 1,4-或 1,5-区域选择性。该方法的实用性进一步通过其与水和空气的相容性、广泛的底物范围、良好的官能团耐受性、克级制备、适用于碳水化合物以及串联的 CuAAC-RhAAC 反应得到了突出体现。
