117734-91-5Relevant academic research and scientific papers
MnO2-Promoted Oxidative Radical Sulfonylation of Haloalkynes with Sulfonyl Hydrazides: C(sp)–S Bond Formation towards Alkynyl Sulfones
Chen, Pengquan,Zhu, Chuanle,Zhu, Rui,Wu, Wanqing,Jiang, Huanfeng
, p. 1875 - 1878 (2017)
A catalyst-free oxidative radical sulfonylation of haloalkynes with sulfonyl hydrazides is reported. It represents an example of C(sp)?S bond formation using sulfonyl hydrazides as sulfonyl radical sources. Various alkynyl sulfones were synthesized in moderate to good yields. Having MnO2 as the oxidant is very critical for this transformation. Remarkably, the self-coupling reaction of haloalkynes through C(sp)?C(sp) bond formation is significantly inhibited under the standard reaction conditions.
Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes
Hammond, Gerald B.,Kumon, Tatsuya,Lu, Zhichao,Umemoto, Teruo
, p. 16171 - 16177 (2021/06/27)
The trifluoromethoxy group has elicited much interest among drug and agrochemical discovery teams because of its unique properties. We developed trifluoromethyl nonafluorobutanesulfonate (nonaflate), TFNf, an easy-to-handle, bench-stable, reactive, and scalable trifluoromethoxylating reagent. TFNf is easily and safely prepared in a simple process in large scale and the nonaflyl part of TFNf can easily be recovered as nonaflyl fluoride after usage and recycled. The synthetic potency of TFNf was showcased with the underexplored synthesis of various trifluoromethoxylated alkenes, through a high regio- and stereoselective hydro(halo)trifluoromethoxylation of alkyne derivatives such as haloalkynes, alkynyl esters, and alkynyl sulfones. The synthetic merits of TFNf were further underscored with a high-yielding and smooth nucleophilic trifluoromethoxylation of alkyl triflates/bromides and primary/secondary alcohols.
Free-Radical Selenosulfonation of Vinylcyclopropanes, a Cyclopropylidene, and Cyclopropylacetylene. Relative Rates of Chain-Transfer, Ring-Opening, and Inversion in Radical Intermediates
Back, Thomas G.,Muralidharan, K. Raman
, p. 121 - 125 (2007/10/02)
The free-radical selenosulfonation of vinylcyclopropanes 4a-e and cyclopropylidene 9 was accompanied by ring-opening to afford 1,5- and 1,3-adducts 7a-e and 11, respectively, whereas cyclopropylacetylene (13) gave predominantly 1,2-addition to afford 15.T
