53034-13-2Relevant articles and documents
Direct Wittig Olefination of Alcohols
Li, Qiang-Qiang,Shah, Zaher,Qu, Jian-Ping,Kang, Yan-Biao
, p. 296 - 302 (2018/02/19)
A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.
Surface-assisted diastereoselective Ullmann coupling of bishelicenes
W?ckerlin, Christian,Li, Jingyi,Mairena, Ana?s,Martin, Kévin,Avarvari, Narcis,Ernst, Karl-Heinz
supporting information, p. 12694 - 12697 (2016/11/02)
Ullmann coupling of chiral 2-bromo[4]helicene has been performed on a Cu(100) surface. Only homochiral 2,2′-bis[4]helicene as the product is observed using STM. Such stereoselectivity is based on the fact that the surface will favour a configuration with
Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig-Heck reaction
Saiyed, Akeel S.,Patel, Krupa N.,Kamath, Bola V.,Bedekar, Ashutosh V.
supporting information; experimental part, p. 4692 - 4696 (2012/09/10)
Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed Heck reaction with arylhalide to give stilbenes as the three-step one-pot sequence.
