Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent

2019 ◽  
Vol 17 (31) ◽  
pp. 7416-7424 ◽  
Author(s):  
Shaohua Jiang ◽  
Zhihai Yang ◽  
Ziyin Guo ◽  
Yibiao Li ◽  
Lu Chen ◽  
...  
Keyword(s):  
Carbon Source ◽  
Transition Metal ◽  
Environmentally Friendly ◽  
Practical Approach ◽  
Reaction Conditions ◽  
Metal Free

A practical approach to the direct α-methylation of 1,8-naphthyridines under mild reaction conditions has been developed using simple and readily available DMSO as a convenient and environmentally friendly carbon source.

scholarly journals Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 696 ◽  
Author(s):  
Pan Zhang ◽  
Jianbin Chen ◽  
Wei Gao ◽  
Yiting Xiao ◽  
Changwei Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Electrode Material ◽  
Environmentally Friendly ◽  
Transition Metal Catalysts ◽  
Reaction Conditions ◽  
Metal Free ◽  
Chemical Oxidants ◽  
Bromide Ion ◽  
Environmentally Friendly Approach ◽  
Graphite Rod

A facile and sustainable electrochemical umpolung of bromide ion protocol was developed under mild reaction conditions. Transition metal catalysts and exogenous chemical oxidants were obviated for the bromination of C–H bond. Notably, graphite rod, which is commercially available at supermarkets and is inexpensive, was employed as the electrode material. This operationally easy and environmentally friendly approach accomplished the synthesis of 3-bromoindole in excellent yield and regioselectivity.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Transition-metal-free arylation of benzoxazoles with aryl nitriles

2018 ◽  
Vol 5 (11) ◽  
pp. 1811-1814 ◽  
Author(s):  
Aizhen Wu ◽  
Quan Chen ◽  
Wei Liu ◽  
Lijun You ◽  
Yifan Fu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Reaction Conditions ◽  
Metal Free ◽  
Simple Reaction ◽  
Aryl Nitriles

Transition-metal-free arylation of benzoxazoles with aryl nitriles has been developed to afford important 2-aryl benzoxazoles under simple reaction conditions.

scholarly journals Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transfer Reaction ◽  
Bond Cleavage ◽  
Electron Transfer Reaction ◽  
Amide Bond ◽  
Single Electron Transfer ◽  
Reaction Conditions ◽  
Metal Free ◽  
Single Electron Transfer Reaction

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

Transition metal-free C(sp3)–H bond coupling among three methyl groups

2017 ◽  
Vol 53 (38) ◽  
pp. 5346-5349 ◽  
Author(s):  
Yufeng Liu ◽  
Xi Zhan ◽  
Pengyi Ji ◽  
Jingwen Xu ◽  
Qiang Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Methyl Groups ◽  
Methyl Ketones ◽  
Reaction Conditions ◽  
Methyl Group ◽  
Metal Free

A coupling of multiple C(sp3)–H bonds of the methyl group in methyl ketones with dimethyl sulfoxides was developed under transition metal-free reaction conditions.

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1805-1809
Author(s):  
Shuai Li ◽  
Xia Wang ◽  
Xin-Ge Yang ◽  
Gui-Quan Yu ◽  
Xue-Qiang Wang
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Wide Range ◽  
Alkyl Ethers

A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested this reaction might take place via nucleophilic aromatic substitution pathway.

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

scholarly journals Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons

2017 ◽  
Vol 8 (1) ◽  
pp. 452-457 ◽  
Author(s):  
Luis Bering ◽  
Andrey P. Antonchick
Keyword(s):  
Transition Metal ◽  
Reaction Conditions ◽  
Saturated Hydrocarbons ◽  
Bond Functionalization ◽  
Metal Free

A selective vicinal dihydroxylation of alkanes by dual C(sp3)–H bond functionalization under transition-metal-free reaction conditions has been developed.

N-Heterocyclic carbene-catalyzed synthesis of functionalized 3-hydroxypyrrolidinones via a domino aza-Michael/aldol reaction

2015 ◽  
Vol 39 (7) ◽  
pp. 5104-5107 ◽  
Author(s):  
Yan-fang Zhu ◽  
Chun Cai
Keyword(s):  
Transition Metal ◽  
Simple Procedure ◽  
Aldol Reaction ◽  
Reaction Conditions ◽  
Metal Free

The reaction features a transition-metal-free approach, mild reaction conditions, as well as a simple procedure.

TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 349-354 ◽  
Author(s):  
Hui-Jing Li ◽  
Yan-Chao Wu ◽  
Yuan-Zhao Ji ◽  
Hao-Ran Yang ◽  
Zheng-Yan Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Reaction Conditions ◽  
Metal Free

A new transition-metal-free route for the direct sulfinylation of electron-rich aromatics with sodium arylsulfinates in the presence of TMSOTf is reported. Various electron-rich aromatics, including pyrroles, thiophenes, indoles, and electron-rich arenes, with sodium arylsulfinates are converted into the corresponding sulfoxides in moderate to excellent yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scopes, and transition-metal-free reaction conditions.

Sign in / Sign up

Export Citation Format

Share Document