Hypervalent iodine(iii) catalyzed oxidative C–N bond formation in water: synthesis of benzimidazole-fused heterocycles

RSC Advances ◽  
2014 ◽  
Vol 4 (49) ◽  
pp. 25600-25604 ◽  
Author(s):  
D. Nageswar Rao ◽  
Sk. Rasheed ◽  
Ram A. Vishwakarma ◽  
Parthasarathi Das
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine ◽  
Ambient Conditions ◽  
Fused Heterocycles

A diverse array of benzimidazole-fused heterocycles was synthesized by in situ generated hypervalent iodine(iii) catalyzed intramolecular oxidative C–N bond formation in water and under ambient conditions.

Synthesis of Benzimidazole-Fused Heterocycles by Intramolecular Oxidative C-N Bond Formation Using Hypervalent Iodine Reagents

Synthesis ◽  
2011 ◽  
Vol 2011 (20) ◽  
pp. 3235-3240 ◽  
Author(s):  
Noriki Kutsumura ◽  
Takao Saito ◽  
Shinichi Kunimatsu ◽  
Kimiko Kagawa ◽  
Takashi Otani
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine ◽  
Fused Heterocycles

ChemInform Abstract: Hypervalent Iodine(III) Catalyzed Oxidative C-N Bond Formation in Water: Synthesis of Benzimidazole-Fused Heterocycles.

ChemInform ◽  
2015 ◽  
Vol 46 (5) ◽  
pp. no-no
Author(s):  
D. Nageswar Rao ◽  
Sk. Rasheed ◽  
Ram A. Vishwakarma ◽  
Parthasarathi Das
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine ◽  
Fused Heterocycles

scholarly journals Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

2019 ◽  
Author(s):  
Felipe Cesar Sousa e Silva ◽  
Nguyen T Van ◽  
Sarah Wengryniuk
Keyword(s):  
Claisen Rearrangement ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

Herein, we report the metal-free direct C–H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of <i>in situ </i>b-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub> reagents, which are readily accessed from the parent iodoarenes. It is tolerant of a wide range of substitution patterns and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.

scholarly journals Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

2019 ◽  
Author(s):  
Felipe Cesar Sousa e Silva ◽  
Nguyen T Van ◽  
Sarah Wengryniuk
Keyword(s):  
Claisen Rearrangement ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

Herein, we report the metal-free direct C–H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of <i>in situ </i>b-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub> reagents, which are readily accessed from the parent iodoarenes. It is tolerant of a wide range of substitution patterns and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.

ChemInform Abstract: Synthesis of Benzimidazole-Fused Heterocycles by Intramolecular Oxidative C-N Bond Formation Using Hypervalent Iodine Reagents.

ChemInform ◽  
2012 ◽  
Vol 43 (8) ◽  
pp. no-no
Author(s):  
Noriki Kutsumura ◽  
Shinichi Kunimatsu ◽  
Kimiko Kagawa ◽  
Takashi Otani ◽  
Takao Saito
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine ◽  
Fused Heterocycles

scholarly journals Oxidative Annulation of Diphenylpropanamides via In Situ Hypervalent Iodine-Promoted Intramolecular C–N/C–O Bond Formation

SynOpen ◽  
2021 ◽  
Vol 05 (04) ◽  
pp. 327-334
Author(s):  
Zhi-Peng Liang ◽  
Ying-Xin Yu ◽  
Yang Wang ◽  
Zheng-Guang Wu ◽  
Yuan-Yuan Sun
Keyword(s):  
Functional Group ◽  
Bond Formation ◽  
Single Step ◽  
Hypervalent Iodine ◽  
Target Compound ◽  
Migration Process ◽  
Aryl Iodide ◽  
Mild Conditions ◽  
Straightforward Approach

AbstractAn aryl iodide catalyzed intramolecular oxidative transformation of diphenylpropanamide derivatives is described that can readily afford the C–N/C–O coupling products in a single step. The speed of the 1,3-aryl iodide migration process determines the diversity of target compound generation in this reaction. This straightforward approach can be performed with the use of inexpensive and readily available catalyst, transition-metal-free, mild conditions and good functional group tolerance.

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

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

scholarly journals Diffusion-induced in situ growth of covalent organic frameworks for composite membranes

2019 ◽  
Vol 7 (45) ◽  
pp. 25802-25807 ◽  
Author(s):  
Priyanka Manchanda ◽  
Stefan Chisca ◽  
Lakshmeesha Upadhyaya ◽  
Valentina-Elena Musteata ◽  
Mark Carrington ◽  
...  
Keyword(s):  
Reaction Times ◽  
Composite Membranes ◽  
Thin Layers ◽  
In Situ Growth ◽  
Covalent Organic Frameworks ◽  
Polymeric Support ◽  
Ambient Conditions ◽  
Induction Method ◽  
Covalent Organic Framework

Thin layers of a covalent organic framework (COF) have been synthesized on a flexible polymeric support using a new diffusion-induction method under ambient conditions in reaction times as short as 3 hours.

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