42036-74-8Relevant articles and documents
Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides
Chen, Hui,Sun, Shuhao,Liao, Xuebin
supporting information, p. 3625 - 3630 (2019/05/24)
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.
Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis
McNulty, James,McLeod, David,Das, Priyabrata,Zepeda-Velázquez, Carlos
, p. 619 - 632 (2016/01/15)
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.
Reactivity of aldehydes with semi-stabilised arsonium ylide anions: Synthesis of terminal (E)-l,3-dienes
Habrant, Damien,Stengel, Bruno,Meunier, Stephane,Mioskowski, Charles
, p. 5433 - 5440 (2008/02/10)
A study of the reactivity of semi-stabilised arsonium ylide anions in olefinalion reactions is presented. The different ylide anions were generated by the addition of nBuLi to various arsonium halide derivatives: [Ph 2As(R)R']+X , where R and R′ are methyl, allyl, prenyl or benzyl groups. By using diallyldiphenylarsonium bromide (R = R′ = allyl) an olefinationprotocol was optimised allowing the efficient transformation of aliphatic aldehydes into terminal 1,3-dienes with a high selectivity for the E isomer (E/Z ratios ranging from 90:10 to 97:3). The olefination reactions of aldehydes with dissymmetric arsonium halides (R≠R′) are very chemoselective; with arsonium ylide anions the benzyl moiety is more reactive than the allyl moiety which is much more reactive than prenyl and methyl groups. Based on the experimental results, a mechanism is proposed for the reaction.
