Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2385-2393 ◽  
Author(s):  
Qiu Sun ◽  
Ling He ◽  
Jiaxin Cheng ◽  
Ze Yang ◽  
Yuansheng Li ◽  
...  
Keyword(s):  
Bond Formation ◽  
Reaction System ◽  
Hypervalent Iodine ◽  
Cascade Process ◽  
One Pot ◽  
Metal Free

A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C–N and C–O bonds and intermolecular C–C bonds from aromatic alkenes or alkynes and N-hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C–H and C–C bonds/construction of C–O bonds/elimination of SO2/C–N bond formation is achieved in sequence­ in the reaction system.

Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Ayesha Jalil ◽  
Yaxin O Yang ◽  
Zhendong Chen ◽  
Rongxuan Jia ◽  
Tianhao Bi ◽  
...  
Keyword(s):  
Natural Products ◽  
Bond Formation ◽  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
The Past ◽  
Oxygen Bond ◽  
Privileged Scaffolds

: Hypervalent iodine reagents are a class of non-metallic oxidants have been widely used in the construction of several sorts of bond formations. This surging interest in hypervalent iodine reagents is essentially due to their very useful oxidizing properties, combined with their benign environmental character and commercial availability from the past few decades ago. Furthermore, these hypervalent iodine reagents have been used in the construction of many significant building blocks and privileged scaffolds of bioactive natural products. The purpose of writing this review article is to explore all the transformations in which carbon-oxygen bond formation occurred by using hypervalent iodine reagents under metal-free conditions

scholarly journals SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

RSC Advances ◽  
2020 ◽  
Vol 10 (29) ◽  
pp. 17288-17292 ◽  
Author(s):  
Yiyong Zhao ◽  
Junjie Wei ◽  
Shuting Ge ◽  
Guofu Zhang ◽  
Chengrong Ding
Keyword(s):  
Transition Metal ◽  
Nitrogen Source ◽  
Functional Group ◽  
Cascade Process ◽  
One Pot ◽  
Metal Free ◽  
Work Up

Our gram-scale process uses abundant and inexpensive aldehydes, a clean nitrogen source, requires no additional carbon atoms, is transition-metal free, and features easy work-up and excellent functional group compatibility.

Transition-Metal-Free Catalysis for the Reductive ­Functionalization of CO2 with Amines

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 548-555 ◽  
Author(s):  
Liang-Nian He ◽  
Xiao-Fang Liu ◽  
Xiao-Ya Li ◽  
Chang Qiao
Keyword(s):  
Transition Metal ◽  
Energy Content ◽  
Bond Formation ◽  
Energy Storage Materials ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
Electron Reduction ◽  
Reduction Of Co2 ◽  
Hierarchical Reduction

Reductive functionalization of CO2 with amines and a reductant, which combines both reduction of CO2 and C–N bond formation in one pot to produce versatile chemicals and energy-storage materials such as formamides, aminals, and methylamines that are usually derived from petroleum feedstock, would be appealing and promising. Herein, we give a brief review on recent developments in the titled CO2 chemistry by employing transition-metal-free catalysis, which can be catalogued as below according to the diversified energy content of the products, that is formamides, aminals, and methylamines being consistent with 2-, 4-, and 6-electron reduction of CO2, respectively. Notably, hierarchical reduction of CO2 with amines to afford at least two products, for example, formamides and methylamines, could be realized with the same catalyst through tuning the hydrosilane type, reaction temperature, or CO2 pressure. Finally, the opportunities and challenges of the reductive functionalization of CO2 with amines are also highlighted.1 Introduction2 2-Electron Reduction of CO2 to Formamide3 6-Electron Reduction of CO2 to Methylamine4 4-Electron Reduction of CO2 to Aminal5 Hierarchical Reduction of CO2 with Amines6 Conclusion

Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C−C Bond Formation

2016 ◽  
Vol 128 (51) ◽  
pp. 16029-16033 ◽  
Author(s):  
Mio Shimogaki ◽  
Morifumi Fujita ◽  
Takashi Sugimura
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine ◽  
Metal Free

scholarly journals Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2525-2538 ◽  
Author(s):  
James Bull ◽  
Renzo Luisi ◽  
Leonardo Degennaro
Keyword(s):  
Transition Metal ◽  
Physicochemical Properties ◽  
Direct Synthesis ◽  
Transition Metal Catalysts ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
New Procedures

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

Metal-Free CN- and NN-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones,N-Tosylhydrazines, and Amines in One Pot

2014 ◽  
Vol 20 (52) ◽  
pp. 17635-17639 ◽  
Author(s):  
Zhengkai Chen ◽  
Qiangqiang Yan ◽  
Zhanxiang Liu ◽  
Yuhong Zhang
Keyword(s):  
Bond Formation ◽  
One Pot ◽  
Metal Free

A one pot, metal-free, three-component domino sequence for the synthesis of furans: an efficient C–O and C–N bond formation approach

RSC Advances ◽  
2016 ◽  
Vol 6 (46) ◽  
pp. 39563-39567 ◽  
Author(s):  
Pengfeng Guo ◽  
Changcheng Wang ◽  
Ya Chen ◽  
Caijun Ou ◽  
Hangqi Jiang ◽  
...  
Keyword(s):  
Aromatic Amine ◽  
Bond Formation ◽  
Domino Reaction ◽  
Aliphatic Acid ◽  
One Pot ◽  
Furan Derivatives ◽  
Dicarbonyl Compounds ◽  
Metal Free

A novel one pot, metal-free, three-component domino reaction for the formation of furan derivatives has been developed from 3-phenylpropiolaldehyde, 1,3-dicarbonyl compounds and aromatic amine or aliphatic acid.

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