123731-28-2Relevant academic research and scientific papers
Ligand-free Cu-catalyzed O-arylation of aliphatic diols
Zheng, Yufen,Zou, Wenxing,Luo, Laichun,Chen, Jiabei,Lin, Songwen,Sun, Qi
, p. 66104 - 66108 (2015/08/18)
Coupling reaction between aryl iodides and aliphatic diols was realized with a ligand-free copper catalyst under mild conditions. This method was successfully applied in the process of scale-up synthesis of medicinal candidate product EMB-3.
Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
supporting information, p. 4747 - 4753 (2014/06/24)
A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
Remarkable solvent effect on Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives: Application to selective and successive removal of allyl, methallyl, and prenyl ethers
Tsukamoto, Hirokazu,Suzuki, Takamichi,Kondo, Yoshinori
, p. 3131 - 3136 (2008/09/19)
Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives in protic polar solvent such as MeOH and aqueous 1,4-dioxane proceeds at room temperature without affecting a wide variety of functional groups. Control of the reaction temperature allows selective and successive cleavage of allyl, methallyl, and prenyl ethers. A study of ligand effects on the deprotection reveals that the improved reactivity in MeOH results from the accelerated oxidative addition to Pd(O). Georg Thieme Verlag Stuttgart.
Facile and selective cleavage of allyl ethers based on palladium(0)-catalyzed allylic alkylation of N,N′-dimethylbarbituric acid
Tsukamoto, Hirokazu,Kondo, Yoshinori
, p. 1061 - 1063 (2007/10/03)
The classical palladium(0)-catalyzed allylic alkylation of N,N′-dimethylbarbituric acid can be applied to the facile and selective cleavage of allylic alkyl ethers to release the corresponding alcohols in excellent yield. This reaction proceeds under neutral conditions without any additive to activate the allyl ethers and tolerates various functional groups, such as ester, ether, ketone, alkyl and aryl chloride, nitrile and nitro groups.
Extremely facile and selective nickel-catalyzed allyl ether cleavage
Taniguchi, Takahiko,Ogasawara, Kunio
, p. 1136 - 1137 (2007/10/03)
Child's play! Allyl ethers as protecting groups for hydroxyl functions can be removed readily with a combination of DIBAL and catalytic amounts of [NiCl2(dppp)]. Propene is expelled in this remarkably selective reaction, and a nickel-catalyzed hydroalumination-elimination pathway is proposed. dppp = propane-1,3-diylbis(diphenylphosphane).
ASYMMETRIC TOTAL SYNTHESES OF (+)- AND (-)-PULO'UPONE
Sugahara, Tsutomu,Iwata, Takashi,Yamaoka, Miyako,Takano, Seiichi
, p. 1821 - 1824 (2007/10/02)
Asymmetric total syntheses of both enantiomers of marine mollusk metabolite pulo'upone 1 have been achieved by Evans' asymmetric Diels-Alder reaction.
