20187-61-5Relevant articles and documents
Gold-catalyzed synthesis of 4-(2-Oxoalkoxy)butyl Methanesulfonates via ring-opening of tetrahydrofuran
Huang, Wangyong,Xiang, Jiannan,He, Weimin
, p. 893 - 894 (2014)
A variety of terminal alkynes were converted into the corresponding 4-(2-oxoalkoxy)butyl methanesulfonates via a gold-catalyzed intermolecular oxidation reaction using 8-ethylquinoline N-oxide as the oxidant and THF as the solvent. This reaction is proposed to proceed through the ring-opening of THF via an α-oxo gold carbene intermediate.
Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
Cui, Xin-Feng,Qiao, Xin,Wang, He-Song,Huang, Guo-Sheng
, p. 13517 - 13528 (2020/12/15)
A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts
Yuki, Yamato,Touge, Taichiro,Nara, Hideki,Matsumura, Kazuhiko,Fujiwhara, Mitsuhiko,Kayaki, Yoshihito,Ikariya, Takao
supporting information, p. 568 - 574 (2017/12/13)
A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).
Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids
Zhang, Yang,Tan, Hua,Liu, Weibing
, p. 54017 - 54020 (2017/12/05)
A simple yet powerful method to synthesize a variety of α-sulfonyloxyketones has been developed. This novel method can be applied for the direct oxysulfonyloxylation of alkynes with sulfonic acids to access a variety of α-sulfonyloxyketones. Compared to the reported methods for the application of PIDA, this study expands its application scope and uses it not only as the oxidant but also as the carrier of O to form the carbonyl group in the products. In addition, under the established conditions, this methodology not only exhibits a broad substrate scope but also demonstrates exclusive regioselectivity with substrates of 1,2-disubstituted internal alkynes.
One-step synthesis of methanesulfonyloxymethyl ketones via gold-catalyzed oxidation of terminal alkynes: A combination of ligand and counter anion enables high efficiency and a one-pot synthesis of 2,4-disubstituted thiazoles
Wu, Gongde,Zheng, Renhua,Nelson, Jonathan,Zhang, Liming
supporting information, p. 1229 - 1234 (2014/05/06)
By using Mor-DalPhos as the P,N-bidentate ligand and mesylate as the counter ion, the resulting gold(I) complex catalyzes efficient oxidative transformations of various terminal alkynes into synthetically versatile methanesulfonyloxymethyl ketones. The mild reaction conditions and high efficiency permit the one-pot synthesis of a range of valuable 2,4-disubstituted thiazoles by subjecting the resulting reaction mixture to a further condensation with thioamides under mild conditions.
Oxidative breakdown of iodoalkanes to catalytically active iodine species: A case study in the α-tosyloxylation of ketones
Guo, Wusheng,Vallcorba, Oriol,Vallribera, Adelina,Shafir, Alexandr,Pleixats, Roser,Rius, Jordi
, p. 468 - 472 (2014/03/21)
Catalysis of the oxidative processes by iodoarenes has become a promising direction in synthesis. The mechanism, involving the well-known isolable hypervalent iodine species, is generally limited to aromatic iodides, since the corresponding aliphatic spec
Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
, p. 5851 - 5854 (2015/01/16)
Using a catalytic amount of 1-iodopropane, a novel and efficient procedure has been developed for direct preparation of α-tosyloxyketones from ketones. In this protocol, 1-iodopropane is first oxidized into iodosylpropane, which decomposes to form the key
Effective α-tosyloxylation of ketones using 1,1,1-trifluoro-2-iodoethane as catalyst
Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
supporting information, p. 3264 - 3270 (2015/10/06)
With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of α-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervale
Straightforward and highly efficient synthesis of α-acetoxy ketones through gold-catalyzed intermolecular oxidation of terminal alkynes
Wu, Chao,Liang, Zhiwu,Yan, Dong,He, Weimin,Xiang, Jiannan
, p. 2605 - 2611 (2013/09/24)
A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O-H insertion.
Gold-catalyzed intermolecular oxidation of terminal alkynes: Simple and efficient synthesis of α-mesyloxy ketones
Xie, Longyong,Liang, Zhiwu,Yan, Dong,He, Weimin,Xiang, Jiannan
supporting information, p. 1809 - 1812 (2013/09/12)
A variety of terminal alkynes were efficiently converted into the corresponding α-mesyloxy ketones through gold-catalyzed intermolecular oxidation in the presence of 3,5-dichloropyridine N-oxide as the oxidant. The reaction is proposed to proceed via α-oxo gold carbene intermolecular O-H insertion. Georg Thieme Verlag Stuttgart · New York.
