1530-11-6Relevant articles and documents
Novel Coupling of Dithioacetals with Grignard Reagents
Ni, Zhi-Jie,Luh, Tien-Yau
, p. 1515 - 1517 (1987)
Dithioacetals react with Grignard reagents in the presence of a catalytic amount of to give the corresponding olefinic coupling products in good yields: a mechanism for the reaction is suggested.
Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes
Zhang, Huaiyuan,Cormanich, Rodrigo A.,Wirth, Thomas
supporting information, (2021/12/22)
Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.
Visible-Light-Induced Meerwein Fluoroarylation of Styrenes
Tang, Hai-Jun,Zhang, Bin,Xue, Fei,Feng, Chao
supporting information, p. 4040 - 4044 (2021/05/26)
An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.
Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate
Cao, Zhi-Chao,Xu, Pei-Lin,Luo, Qin-Yu,Li, Xiao-Lei,Yu, Da-Gang,Fang, Huayi,Shi, Zhang-Jie
supporting information, p. 781 - 785 (2019/06/24)
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.
Ruthenium(II)-catalyzed olefination: Via carbonyl reductive cross-coupling
Wei, Wei,Dai, Xi-Jie,Wang, Haining,Li, Chenchen,Yang, Xiaobo,Li, Chao-Jun
, p. 8193 - 8197 (2017/11/27)
Natural availability of carbonyl groups offers reductive carbonyl coupling tremendous synthetic potential for efficient olefin synthesis, yet the catalytic carbonyl cross-coupling remains largely elusive. We report herein such a reaction, mediated by hydrazine under ruthenium(ii) catalysis. This method enables facile and selective cross-couplings of two unsymmetrical carbonyl compounds in either an intermolecular or intramolecular fashion. Moreover, this chemistry accommodates a variety of substrates, proceeds under mild reaction conditions with good functional group tolerance, and generates stoichiometric benign byproducts. Importantly, the coexistence of KOtBu and bidentate phosphine dmpe is vital to this transformation.
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Brown, Michael,Kumar, Ravi,Rehbein, Julia,Wirth, Thomas
supporting information, p. 4030 - 4035 (2016/03/16)
A stereoselective hypervalent iodine-promoted oxidative rearrangement of 1,1-disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched α-arylated ketones without the use of transition metals from readily
Metal-Free Microwave-Assisted Decarboxylative Elimination for the Synthesis of Olefins
Wu, Shu-Wei,Liu, Jia-Li,Liu, Feng
supporting information, p. 1 - 3 (2016/01/15)
A metal-free efficient synthesis of olefins via microwave-assisted direct decarboxylative elimination of arylacetic acids is described. This reaction, using commercially available reagent PIFA as oxidant, readily provides a variety of desired products in moderate to good yields.
Copper-catalyzed aerobic aliphatic C-H oxygenation with hydroperoxides
Too, Pei Chui,Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 1217 - 1225 (2013/07/26)
We report herein Cu-catalyzed aerobic oxygenation of aliphatic C-H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carboncentered radicals with molecular oxygen.
A 1,3-sp2,sp3-hybridized dilithio intermediate by direct lithiation of cyclopropylidene diphenylmethane
Lillo, Victor J.,Gomez, Cecilia,Yus, Miguel
experimental part, p. 29 - 44 (2010/08/20)
The reaction of cyclopropylidene diphenylmethane 1 with an excess of lithium and a catalytic amount of naphthalene (5 mol %) at -20°, followed by addition of an electrophile [E = H2O, D2O, t-BuCHO, Me2CO, Et2CO,
Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids
Zhao, Xia,Jing, Jing,Lu, Kui,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 1724 - 1726 (2010/07/06)
The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.
