22174-59-0Relevant articles and documents
Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid
Fan, Chao,Hou, Jing,Chen, Yu-Jia,Ding, Kui-Ling,Zhou, Qi-Lin
supporting information, p. 2074 - 2077 (2021/04/05)
A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.
Electrochemical properties and reactions of organoboronic acid esters containing unsaturated bonds at their α-position
Ohtsuka, Kazuhiro,Inagi, Shinsuke,Fuchigami, Toshio
, p. G23 - G28 (2017/12/26)
Electrochemical analyses of 2-(cynnamyl)boronic acid pinacol ester and (3-phenyl-2-propynyl)boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We
A highly efficient and recyclable Pd(PPh3)4/PEG-400 system for Stille cross-coupling reactions of organostannanes with aryl bromides
Huang, Xue,Yao, Fang,Wei, Ting,Cai, Mingzhong
, p. 547 - 550 (2017/10/03)
Pd(PPh3)4 in PEG-400 is shown to be a highly efficient catalyst for the Stille cross-coupling reactions of various organotin compounds with aryl bromides. The reaction could be conducted at 80 °C using NaOAc as base, yielding a variety of biaryls, alkynes and alkenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether and the Pd(PPh3)4/PEG-400 system could be easily recycled and reused five times without any significant loss of activity.
Metal-free iodine(III)-promoted synthesis of isoquinolones
Chen, Zhi-Wei,Zhu, Yi-Zhou,Ou, Jin-Wang,Wang, Ya-Ping,Zheng, Jian-Yu
, p. 10988 - 10998 (2015/01/08)
A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared via oxidative annulation of simple N-methoxybenzamide and diarylacetylene or aryl/alkyl acetylene derivatives in yields up to 87%.
A practical synthesis of biaryls and aromatic acetylenes by stille coupling in room-temperature ionic liquids
Hao, Wenyan,Xi, Zhiwen,Cai, Mingzhong
experimental part, p. 2396 - 2406 (2012/06/18)
The Stille cross-coupling reactions of aryl halides with aryl or alkynylstannanes have been achieved under mild conditions in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]), affording the corresponding biaryls and aromatic acetylenes in good yields. Use of this solvent allows for facile recycling of the solvent and catalyst system, which can be used at least five times without loss of activity.
Iron(II) chloride catalyzed alkylation of propargyl ethers: Direct functionalization of an sp3 C-H bond adjacent to oxygen
Xie, Yongju,Yu, Ming,Zhang, Yuhong
supporting information; experimental part, p. 2803 - 2809 (2011/10/09)
Iron(II) chloride catalyzed direct alkylation of sp3 C-H bond adjacent to oxygen in propargyl ethers has been accomplished by the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant under mild reaction conditions. The reaction proceeded smoothly with a variety of 1,3-diketones leading to -dicarbonyl ether in moderate yields. In the absence of 1,3-diketones, ynenones were produced by the use of iron(III) chloride and DDQ. Georg Thieme Verlag Stuttgart - New York.
Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals
Vo, Cam-Van T.,Mitchell, T. Andrew,Bode, Jeffrey W.
supporting information; experimental part, p. 14082 - 14089 (2011/10/12)
Mixed acetals and organotrifluoroborates undergo BF3· OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF 3·OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 °C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.
Studies on Cu(I)-catalyzed synthesis of simple 3-substituted 1,2-allenes and optically active 2-substituted secondary 2,3-allenols
Li, Jing,Zhou, Chao,Fu, Chunling,Ma, Shengming
experimental part, p. 3695 - 3703 (2009/09/05)
The sequential treatment of terminal alkynes or propargylic alcohols with n-BuLi and MOMCl afforded the corresponding propargylic methyl ethers, which would react with primary alkyl Grignard reagents under the catalysis of CuBr to afford 3-substituted 1,2-allenes or 2-substituted secondary 2,3-allenols, respectively. The reaction may be applied to the synthesis of optically active 2-substituted secondary 2,3-allenols with up to >99% ee without any protection to the free hydroxyl group in the starting 4-hydroxy-2-alkynyl methyl ethers.
Synthesis of dialkyl ethers from organotrifluoroborates and acetals
Mitchell, T. Andrew,Bode, Jeffrey W.
supporting information; experimental part, p. 18057 - 18059 (2010/03/26)
(Chemical Equation Presented) The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3?OEt2
MCM-41-supported bidentate phosphine palladium(0) complex as an efficient catalyst for the heterogeneous Stille reaction
Zhao, Hong,Wang, Yue,Sha, Junchao,Sheng, Shouri,Cai, Mingzhong
, p. 7517 - 7523 (2008/12/20)
A Stille coupling reaction of organostannanes with organic halides has been developed in the presence of a catalytic amount of MCM-41-supported bidentate phosphine palladium(0) complex (0.5 mol %) in DMF/H2O (9:1) under air atmosphere in high yields. This polymeric palladium catalyst exhibits higher activity than Pd(PPh3)4 and can be reused at least 10 times without any decrease in activity.
