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Upstream product

• 112-54-9 Dodecanal 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 105-74-8 dilauryl peroxide 
• 536-74-3 phenylacetylene 
• 645-66-9 lauric anhydride 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 588-73-8 (Z)-β-bromostyrene 

Relevant academic research and scientific papers

Highly Stereoselective and General Synthesis of (E)-Stilbenes and Alkenes by Means of an Aqueous Wittig Reaction

The chemoselective formation of trialkyl(benzylidene) ylides in water and their Wittig reaction with aromatic and. aliphatic aldehydes provides a practical, stereoselective and environmentally benign route to valuable (E)-stilbenes and alkenes. The synthesis of the phytoalexin resveratrol is described, J.n addition, the method allows for a gram-scale synthesis of the anticancer agent DMU-212 utilizing no organic solvent at any stage. Wiley-VCH Verlag GmbH & Co. KGaA.

Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides

Decarboxylative cross-coupling of aliphatic acid anhydrides with vinyl triflates or halides was accomplished via nickel catalysis. This methodology works well with a broad array of substrates and features abundant functional group tolerance. Notably, our approach addresses the issue of safe and environmental installation of methyl or ethyl group into molecular scaffolds. The method possesses high chemoselectivity toward alkyl groups when aliphatic/aromatic mixed anhydrides are involved. Furthermore, diverse ketones could be modified with our strategy.

Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides

A photo and nickel co-catalyzed hydroalkylation of terminal aryl alkynes enabled Z-preferred olefin synthesis has been developed under mild conditions. Alkyl diacyl peroxides were utilized as a new type of alkylation reagents and afforded Z-olefins as the major products in moderate to good yields.

Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis

The development of semi-stabilized, stabilized, and functionalized ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy separation of water-soluble phosphine oxides. The development of a mild organocatalytic process for the Wittig reaction and extension toward the preparation of reporter stilbenes under biological conditions are also described. Applications toward the preparation of biologically active natural products and derivatives are discussed.

Wittig Reagents Bound to Cross-Linked Polystyrenes

Insoluble benzyltriarylphosphonium and methyltriarylphosphonium salts have been prepared on 2percent and 8percent divinylbenzene cross-linked polystyrene and on 20percent divinylbenzene cross-linked macroporous polystyrene.Phosphoranes were generated with sodium methoxide or sodium ethoxide in THF and with the dimethylsulfinyl carbanion in Me2SO from the benzyl- and methylphosphonium salts, respectively.Reactions of the phosphoranes with a variety of aldehydes and ketones provided alkenes in 73-96percent yields (by GLC analysis) with the 2percent cross-linked polymer, 52-77percent yields with the 8percent cros s-linked polymer, and 72-87percent yields with the 20percent cross-linked macroporous polymer.The rates of phosphorane generation and alkene formation depend on the polymer, decreasing in the order 2percent > 20percent macroporous > 8percent cross-linked.The fraction of E double bond product from the benzylphosphonium salt and either benzaldehyde or cinnamaldehyde is greater with the 20percent cross-linked macroporous polymer than with the 2percent cross-linked polymer.The byproduct polymer-bound phosphine oxides were reduced to phosphines with trichlorsilane, and the phosphines were reused for Wittig synthesis.A quantitative 31P-NMR analysis of phosphine and phosphine oxide residues in polystyrene gels is reported.