- Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones
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Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
- Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
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supporting information
p. 18039 - 18042
(2021/11/16)
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- Synthesis method of alpha-carbonyl sulfonate and catalyst used in synthesis method
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The invention provides a nitrogen and carbon co-doped Nb2O5 catalyst for synthesizing alpha carbonyl sulfonate, a preparation method of the nitrogen and carbon co-doped Nb2O5 catalyst, and a synthesizing method of the alpha carbonyl sulfonate by using the catalyst under the driving of visible light. Based on the total weight of the catalyst, the content of nitrogen is 0.01 wt%-1wt%; the content of the carbon is 0.01 wt% to 1.5 wt%. The catalyst provided by the invention is used for preparing alpha-carbonyl sulfonate through olefin aerobic oxidation, the reaction condition is mild, oxygen is used as an oxidant, and other oxidants are not needed. All the raw materials of the catalyst are rich in resource and low in price, and the catalyst can be recycled without inactivation and is very stable to air, water and heat.
- -
-
Paragraph 0076-0086
(2021/04/17)
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- Facile synthesis of polysubstituted cyclopropanes using α-tosyloxyketones
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A facile synthesis of polysubstituted cyclopropanes (5) by the treatment of pyridinium ylides, generated in situ from pyridinium toslyates (2), with arylidenemalonitrile (4) is presented. Pyridinium toslyates (2) were obtained by reacting α-tosyloxyketone
- Rana, Neena,Nain, Sonia,Kumar, Dinesh,Kumar, Ravi
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p. 505 - 507
(2018/02/09)
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- Metal-free C(sp3)-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones
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Pyridin-2-ylmethyl tosylate derivatives are obtained in high yields from 2-alkylpyridine 1-oxides via a [3,3]-sigmatropic rearrangement of the adduct between 2-alkylpridine 1-oxides with benzenesulfonyl chlorides. Moreover, alkylnitrones also undergo [3,3]-sigmatropic rearrangement to give α-tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.
- Wang, Chang-Sheng,Dixneuf, Pierre H.,Soulé, Jean-Fran?ois
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p. 4954 - 4957
(2018/07/25)
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- α-tosyloxyketones as versatile synthetic equivalents to α-Haloketones: Facile synthesis of disubstituted oxazoles
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A facile synthesis of disubstituted oxazoles (3) in good yields via decarboxylative oxidative cyclization of primary amino acids (1) and α-tosyloxyketones (2) is described.
- Neena,Nain, Sonia,Kumar, Dinesh,Kumar, Ravi
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p. 107 - 112
(2019/01/18)
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- A convenient [hydroxy(tosyloxy)iodo]benzene-mediated one-pot synthesis of 2-arylimidazo[2,1-b[benzothiazoles
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Several 2-arylimidazo[2,1-b]benzothiazoles (4) have been conveniently synthesized in one-pot reactions via α-tosyloxylation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene 2 in acetonitrile, followed by treatment with 2-amino-6-(substituted
- Sumran, Garima,Aggarwal, Ranjana
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p. 170 - 177
(2015/10/20)
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- Oxidative breakdown of iodoalkanes to catalytically active iodine species: A case study in the α-tosyloxylation of ketones
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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
- Guo, Wusheng,Vallcorba, Oriol,Vallribera, Adelina,Shafir, Alexandr,Pleixats, Roser,Rius, Jordi
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p. 468 - 472
(2014/03/21)
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- Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
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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
- Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
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p. 5851 - 5854
(2015/01/16)
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- 2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable "iodoarene" for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones
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The synthesis of 2,4,6-tris[(4-iodo)phenoxy)]-1,3,5-triazine 6, as a new recyclable nonpolymeric analogue of iodobenzene is achieved using the reaction of 2,4,6-trichloro-1,3,5-triazine with 4-iodophenol in the presence of KOH. The application of 6 as a r
- Thorat, Prerana B.,Bhong, Bhagyashree Y.,Shelke, Amol V.,Karade, Nandkishor N.
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p. 3332 - 3335
(2014/06/09)
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- Effective α-tosyloxylation of ketones using 1,1,1-trifluoro-2-iodoethane as catalyst
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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
- Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
-
supporting information
p. 3264 - 3270
(2015/10/06)
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- Modified one-pot multicomponent diastereoselective synthesis of trans-2,3-Dihydrofuro[3,2-c]coumarins via in situ-generated α- tosyloxyketones
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A modified protocol for diastereoselective synthesis of differently substituted trans-2,3-dihydrofuro[3,2-c]coumarins is developed via, a one-pot multicomoponent reaction starting from aromatic aldehydes, 4-hydroxycoumarin, and α-tosyloxyacetophenones wit
- Kumar, Ravi,Wadhwa, Deepak,Hussain, Khalid,Prakash, Om
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p. 1802 - 1807
(2013/05/22)
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- Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones
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New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with
- Guo, Wusheng,Monge-Marcet, Amàlia,Catto?n, Xavier,Shafir, Alexandr,Pleixats, Roser
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p. 192 - 199
(2013/02/25)
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- Iodine-mediated α-sulfonyloxylation of alkyl aryl ketones with oxone and sulfonic acids
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Alkyl aryl ketones are converted into the corresponding α-sulfonyloxyketones, in moderate to excellent yields, via a novel procedure that utilizes Oxone, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of aceton
- Kikui, Hiroki,Moriyama, Katsuhiko,Togo, Hideo
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p. 791 - 797
(2013/04/10)
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- An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot
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An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation. Website
- Li, Xiaoqing,Zhou, Can,Hu, Zhiyan,Xu, Xiangsheng
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p. 579 - 581
(2013/10/22)
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- A novel one-pot method for αα-tosyloxylation of ketones using a catalytic amount of ammonium iodide
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A novel one-pot procedure was designed for the preparation of various α-tosyloxy ketones in good yields by the reaction of ketones with m-chloroperoxybenzoic acid and p-toluenesulfonic acid monohydrate in the presence of catalytic amounts of ammonium iodi
- Hu, Jiantao,Zhu, Min,Xu, Yuan,Yan, Jie
-
experimental part
p. 1226 - 1232
(2012/05/20)
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- Catalytic, asymmetric, interrupted Feist-Benary reactions of α-tosyloxyacetophenones
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A new variant of the Interrupted Feist-Benary (IFB) reaction uses α-tosyloxyacetophenones as electrophiles and proceeds in good yields and excellent enantioselectivities.
- Calter, Michael A.,Korotkov, Alexander
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supporting information; experimental part
p. 6328 - 6330
(2012/01/11)
-
- Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant
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Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant is described. The method is simple, rapid and practical, generating α-azidoketones and α-thiocyanatoketones from the aryl ketone without
- Chang, Ya-Li,Chung, Chi-Lin,Wu, Fang-Wen,Wang, Huey-Min,Hou, Rei-Sheu,Kang, Iou-Jiun,Chen, Ling-Ching
-
experimental part
p. 149 - 152
(2011/04/16)
-
- Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA in ionic liquid
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Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA as a cooxidant in ionic liquid is described. The method is simple, rapid and practical, generating Imidazo[1,2-a]pyridines from the aryl ketone without isolation of α-
- Chang, Ya-Li,Wang, Huey-Min,Hou, Rei-Sheu,Kang, Iou-Jiun,Chen, Ling-Ching
-
experimental part
p. 153 - 156
(2011/04/16)
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- Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and Na2S·9H20
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An efficient method for the preparation of symmetrical diketosulfides of the type ArCOCH2SCH2COAr has been developed from the reaction of [hydroxy(tosyloxy)iodo]benzene with various acetophenones, followed by treatment with Na2
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.,Shinde, Sandeep V.
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experimental part
p. 172 - 176
(2009/09/30)
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- Synthesis of 2,5-disubstituted 1,3,4-oxadiazine and 1,3,4-thiadiazine from substituted acetophenones and acid hydrazides using [Hydroxyl(tosyloxy)iodo] benzene
-
A novel and direct method for the efficient synthesis of 2,5-disubstituted 1,3,4-oxadiazines from the reactions of [hydroxy(tosyloxy)iodo]benzene with substituted acetophenones, followed by the treatment with acid hydrazide and K2CO3, is reported. The met
- Karade, Nandkishor N.,Kondre, Jeevan M.,Gampawar, Sumeet V.,Shinde, Sandeep V.
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experimental part
p. 2279 - 2287
(2009/12/03)
-
- α-Tosyloxylation of ketones with ion-supported[hydroxy(tosyloxy)iodo] benzene
-
A new room-temperature ionic liquid (RTIL) supported [hydroxy(tosyloxy) iodo]benzene (ion-supported HTIB) reagent was synthesised by three kinds of effective methods in high yields, which combined the advantages of ionic liquids and the hypervalent iodine
- Su, Feng,Zhang, Jizhen,Jin, Guangyu,Qiu, Tao,Zhao, Dejian,Jia, Hongbin
-
experimental part
p. 741 - 744
(2010/03/24)
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- One-pot synthesis of α-formyloxy ketones from enolizable ketones
-
One-pot synthesis of α-formyloxy tones as well as α-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy) iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy) iodo] benzene (PSHTIB) in N,N-dimethylformamide (DMF)/N, N-dimethylacetamide (DMA)
- Kumar, Sunil,Kumar, Ashok,Gupta, Rakesh K.,Kumar, Devinder
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p. 338 - 345
(2008/04/01)
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- Solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one from Dess-Martin periodinane and its synthetic utility for α-tosyloxylation of ketones
-
The solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one is reported from Dess-Martin periodinane and p-toluenesulfonic acid monohydrate using a grinding technique and is subsequently utilized for the α-tosyloxylation of a range of enolisable ketones.
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Shinde, Sandeep V.,Gampawar, Sumeet V.,Kondre, Jeevan M.
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p. 3441 - 3443
(2008/09/21)
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- [Hydroxy(tosyloxy)iodo]benzene mediated α-azidation of ketones
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Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by using iodosobenzene in combination with p-toluene-sulphonic acid.
- Prakash, Om,Pannu, Kamaljeet,Prakash, Richa,Batra, Anita
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p. 523 - 527
(2007/10/03)
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- Hypervalent iodine in the synthesis of bridgehead heterocycles: A facile route to the synthesis of 6-arylimidazo[2,1-b]thiazoles using [hydroxy(tosyloxy)iodo]benzene
-
α-Tosyloxyketones (2), readily accessible through hypervalent iodine oxidation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, exclusively generates the 6-arylimidazo[2,1-b]thiazoles (4) on treatment with commerciall
- Aggarwal, Ranjana,Sumran, Garima
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p. 875 - 879
(2007/10/03)
-
- A facile [hydroxy(tosyloxy)iodo]benzene mediated synthesis of 2-arylimidazo[1,2-a]pyrimidines and their conversion into 3-bromo-2- arylimidazo[1,2-a]pyrimidines
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α-Tosyloxyketone 2, obtained through hypervalent iodine oxidation of enolizable ketones using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, on treatment with 2-aminopyrimidine 3 generates regioselectively 2-arylimidazo[1,2-a]pyrimidine 6 which up
- Aggarwal, Ranjana,Sumran, Garima
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p. 2690 - 2695
(2007/10/03)
-
- Use of [hydroxy(tosyloxy)iodo]benzene in a novel and facile synthesis of 1,4-diaryl-2-(arylamino)but-2-ene-1,4-diones
-
The reaction of acetophenones 1 with [hydroxy(tosyloxy)iodo]benzene followed by treatment of the resulting α-tosyloxyacetophenones 2 thus formed with anilines 3 in the presence of sodium carbonate in ethanol provides a novel one-pot synthesis of 1,4-diary
- Prakash, Om,Batra, Anita,Chaudhri, Vishwas,Prakash, Richa
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p. 2877 - 2878
(2007/10/03)
-
- A facile synthesis of thiazole-2(3H)-thiones through [hydroxy(tosyloxy) iodo]benzene
-
A one-pot facile synthesis of thiazole-2(3H)-thiones (4) has been achieved by hypervalent iodine oxidation of ketones (1) using [hydroxy (tosyloxy)iodo]benzene, followed by the treatment of the reaction mixture with dithiocarbamate salts (3) The intermediate α-tosyloxy-ketones (2) have also been isolated and converted to the target compounds.
- Aggarwal, Ranjana,Pundeer, Rashmi,Kumar, Vinod,Chaudhri, Vishwas,Singh, Shiv P.,Prakash, Om
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p. 2659 - 2664
(2007/10/03)
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- Efficient oxidation of benzylic alcohols with [hydroxy(tosyloxy)iodo] benzene under microwave irradiation
-
An efficient method for the oxidation of benzylic alcohols with [hydroxy(tosyloxy)iodo]benzene under solvent-free microwave irradiation conditions is described.
- Lee, Jong Chan,Lee, Ji Young,Lee, Seung Jun
-
p. 4939 - 4941
(2007/10/03)
-
- Organic reactions in ionic liquids: α-tosyloxylation of ketones
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The room temperature ionic liquid, n-butylpyridinium tetrafluoroborate (BPyBF4) is used as a ''green'' recyclable alternative to classical molecular solvents for the α-tosyloxylation of ketones.
- Xie, Yuan Xie,Chen, Zhen Chu,Zheng, Qin Guo
-
p. 618 - 619
(2007/10/03)
-
- Organic reactions in ionic liquids: Ionic liquid-accelerated cyclocondensation of α-tosyloxyketones with 2-aminopyridine
-
The room temperature ionic liquid n-butylpyridinium tetrafluoroborate (BPyBF4) is used as a 'green' recyclable alternative to classical molecular solvents for the cyclocondensation of α-tosyloxyketones with 2-aminopyridine. Significant rate enh
- Xie, Yuan-Yuan,Chen, Zhen-Chu,Zheng, Qin-Guo
-
p. 1505 - 1508
(2007/10/03)
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- Hypervalent iodine in synthesis. 48. A one-pot convenient procedure for the synthesis of 2-mercaptothiazoles by cyclocondensation of ketones with [hydroxy(tosyloxy)iodo]-benzene and ammonium dithiocarbamate
-
α-Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]-benzene (HTIB), followed by treatment with ammonium dithiocarbamate, provides a one-pot convenient procedure for the synthesis of 2-mercaptothiazoles with good yields.
- Zhang,Chen
-
p. 415 - 420
(2007/10/03)
-
- Hypervalent iodine in synthesis 81: A one-pot procedure for the synthesis of 1H-imidazole derivatives by cyclocondensation of ketones with [Hydroxy(tosyloxy)iodo]benzene and amidines
-
Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB), followed by treatment with amidines provides a one-pot procedure for the synthesis of 1H-imidazole derivatives with good yields.
- Zhang,Chen
-
p. 2075 - 2077
(2007/10/03)
-
- Some hypervalent iodine(III) mediated solid-state transformations
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Some known hypervalent iodine(III) mediated reactions, viz (i) dimerization of acid hydrazides 1a-i, (ii) α-tosyloxylation of acetophenones 3a-f, and (iii) α-hydroxylation of acetophenones 3c,d,f have been effected in solid-state.
- Prakash, Om,Sharma, Vijay
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p. 229 - 231
(2007/10/03)
-
- Bridgehead Nitrogen Heterocycles: Facile Synthesis of Imidazo -1,3,4-Thiadiazoles Using Hypervalent Iodine
-
2,6 Diarylimidazo -1,3,4 thiadiazoles (3) were synthesized by reactions of either α-haloketones with 2-aminothiadiazoles (1) or directly with acetophenones in the presence of benzene.The latter method is convenient and vers
- Mohan, Jag,Singh, Virender,Kataria, Sangeeta
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p. 617 - 619
(2007/10/03)
-
- A novel thallium(III) - mediated approach to 2-substituted thiazoles from enolizable ketones
-
Treatment of thallium (III) p-tolylsulphonate (TTS) with enolizable ketones (1) in refluxing acetonitrile or dioxane followed by addition of thiourea or thioamides provides a novel approach for the synthesis of 2-substituted thiazoles (3).
- Khanna, Mahavir S.,Garg, Chandra P.,Kapoor, Ram P.
-
-
- Hypervalent iodine oxidation: A facile access to α-thiocyanatoketones
-
Aryl alkyl ketones (1) on treatment with benzene or benzene undergo oxidation via α-sulphonyloxyketones as intermediates to form α-thiocyanoketones (2) in excellent yields.
- Khanna, Mahavir S.,Sangeeta,Garg, Chandra P.,Kapoor, Ram P.
-
-
- α-tosyloxylation of enolizable ketones using thallium(III)p-tolylsulphonate (TTS)
-
Thallium(III)p-torylsulphonate(TTS) in refluxing acetonitrile provides a new useful one step conversion of enolizable ketones to α-tosyloxy ketones. α-Tosyloxylation of enolizable ketones using Thallium(III)p-torylsulphonate (TTS) in refluxing acetonitril
- Khanna, Mahavir S.,Garg, Chandra P.,Kapoor, Ram P.
-
p. 1495 - 1498
(2007/10/02)
-
- A convenient synthesis of α-anilinoacetophenones using hypervalent iodine
-
Hypervalent iodine oxidation of acetophenones (1) with benzene, followed by treatment with appropriate aniline, provides a new, convenient and useful route to the synthesis of α-anilinoacetophenones (3a-h).
- Prakash, Om,Rani, Neena,Goyal, Seema
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p. 349 - 350
(2007/10/02)
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- Hypervalent Iodine in the Synthesis of Bridgehead Heterocycles: Novel and Facile Syntheses of 3-Substituted-5,6-Dihydroimidazothiazoles and 3-Phenylthiazolobenzimidazole from Acetophenones using benzene
-
The synthesis of 3-substituted-5,6-dihydroimidazothiazoles 3a-f has been achieved by using a novel and facile method involving hypervalent iodine oxidation of acetophenones 1a-f with benzene, followed by the treatment of the
- Prakash, Om,Rani, Neena,Goyal, Seema
-
p. 707 - 710
(2007/10/02)
-