20608-83-7Relevant articles and documents
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
supporting information, p. 24284 - 24291 (2021/10/08)
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
Transition-Metal-Free Heterobiaryl Synthesis via Aryne Coupling
Saied, Tarak,Demangeat, Catherine,Panossian, Armen,Leroux, Frédéric R.,Fort, Yves,Comoy, Corinne
supporting information, p. 5275 - 5284 (2019/03/27)
We disclose, for the first time, an efficient route for the construction of various heterobiaryl backbones in fair to excellent yields using the Aryne coupling methodology. This study outlined the remarkable effect of external chelating ligands and salt additives on the heterocyclic partner reactivity in the aryne coupling reaction.
Rhodium-catalyzed intramolecular C-H silylation by silacyclobutanes
Zhang, Qing-Wei,An, Kun,Liu, Li-Chuan,Guo, Shuangxi,Jiang, Chenran,Guo, Huifang,He, Wei
supporting information, p. 6319 - 6323 (2016/05/24)
Silacyclobutane was discovered to be an efficient C-H bond silylation reagent. Under the catalysis of RhI/TMS-segphos, silacyclobutane undergoes sequential C-Si/C-H bond activations, affording a series of π-conjugated siloles in high yields and regioselectivities. The catalytic cycle was proposed to involve a rarely documented endocyclic β-hydride elimination of five-membered metallacycles, which after reductive elimination gave rise to a Si-RhI species that is capable of C-H activation. Old reagent, new reactivity: Silacyclobutane was discovered to be an efficient C-H bond silylation reagent under the catalysis of Rh/TMS-segophos. This new reactivity was attributed to a key Si-RhI intermediate formed through a Si-C activation, endocyclic β-H elimination and reductive elimination cascade. A wide array of siloles was obtained in high yields and excellent regioselectivities.
