35737-41-8Relevant academic research and scientific papers
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
supporting information, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light
Liu, Peng,Liu, Wenbo,Li, Chao-Jun
supporting information, p. 14315 - 14321 (2017/10/17)
The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group
Brown, Michael D.,Whitham, Gordon H.
, p. 817 - 822 (2007/10/02)
The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.
