Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Synthesis ◽  
2020 ◽  
Author(s):  
Mei Guan ◽  
Yong Wu ◽  
Hua He ◽  
Kaichuan Yan ◽  
Jianglian Li ◽  
...  
Keyword(s):  
Organic Solvents ◽  
Bioactive Compounds ◽  
Late Stage ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Significant Development ◽  
Metal Free ◽  
Water As Solvent ◽  
Mild Temperature

Carbenoid-based N–H insertions have undergone significant development with respect to C–N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

Transition metal-free aroylation of NH-sulfoximines with methyl arenes

2015 ◽  
Vol 51 (80) ◽  
pp. 14889-14892 ◽  
Author(s):  
Ya Zou ◽  
Jing Xiao ◽  
Zhihong Peng ◽  
Wanrong Dong ◽  
Delie An
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Metal Free

An iodine-catalyzed N-aroylation of NH-sulfoximines with methyl arenes was herein demonstrated without participation of external organic solvents, transition metal-catalysts or ligands.

Oxidative cross dehydrogenative coupling between iodoarenes and acylanilides for C–N bond formation under metal-free conditions

2021 ◽  
Author(s):  
Peng Yang ◽  
Xia Wang ◽  
Liang Wang ◽  
Jiahua He ◽  
Qian Zhang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Metal Catalysts ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Formation Method

A novel metal-free C–N bond formation method through oxidative cross dehydrogenative coupling between iodoarenes and acylanilides was developed. The reaction was mediated by mCPBA without any metal catalysts or additives....

Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Biologically Active ◽  
Dft Studies ◽  
Thermodynamic Control ◽  
Important Goal ◽  
Peptide Bonds ◽  
Metal Free ◽  
Vinyl Cation ◽  
E And Z Isomers ◽  
Vinyl Fluorides

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>

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 Kinetic resolution of indolines by asymmetric hydroxylamine formation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Gang Wang ◽  
Ran Lu ◽  
Chuangchuang He ◽  
Lei Liu
Keyword(s):  
Hydrogen Peroxide ◽  
Chemical Synthesis ◽  
Late Stage ◽  
Kinetic Resolution ◽  
High Efficiency ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Environmentally Benign ◽  
Secondary Amines

AbstractCatalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N–O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules that are otherwise difficult to synthesize was also explored.

scholarly journals Chemoselective bioconjugation based on modular click chemistry with 4-halocoumarins and aryl sulfonates

RSC Advances ◽  
2021 ◽  
Vol 11 (31) ◽  
pp. 18960-18965
Author(s):  
F. Yushra Thanzeel ◽  
Christian Wolf
Keyword(s):  
Click Chemistry ◽  
Bond Formation ◽  
Metal Free

We report chemoselective and modular peptide bioconjugation using stoichiometric amounts of 4-halocoumarin and arylsulfonate agents that undergo metal-free C(sp2)-heteroatom bond formation at micromolar concentrations.

Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)2-Mediated Oxidative C–C Bond Formation

2014 ◽  
Vol 79 (3) ◽  
pp. 1111-1119 ◽  
Author(s):  
Jinglei Lv ◽  
Daisy Zhang-Negrerie ◽  
Jun Deng ◽  
Yunfei Du ◽  
Kang Zhao
Keyword(s):  
Bond Formation ◽  
Metal Free
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