Metal-Free Intramolecular Aziridination of Allylic Carbamates Mediated by Hypervalent Iodine Compounds

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.

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

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x17999200807140943 ◽

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

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Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽

10.3390/molecules26071897 ◽

2021 ◽

Vol 26 (7) ◽

pp. 1897

Author(s):

Hideyasu China ◽

Nami Kageyama ◽

Hotaka Yatabe ◽

Naoko Takenaga ◽

Toshifumi Dohi

Keyword(s):

Aqueous Solution ◽

Room Temperature ◽

Practical Method ◽

Hypervalent Iodine ◽

Mild Conditions ◽

Sequential Procedures ◽

Iodine Compounds ◽

Practical Synthesis ◽

Iodosobenzoic Acid ◽

Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

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Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions

New Journal of Chemistry ◽

10.1039/c4nj01668h ◽

2015 ◽

Vol 39 (2) ◽

pp. 805-809 ◽

Cited By ~ 21

Author(s):

Nagireddy Veera Reddy ◽

Pailla Santhosh Kumar ◽

Peddi Sudhir Reddy ◽

Mannepalli Lakshmi Kantam ◽

Kallu Rajender Reddy

Keyword(s):

Cross Coupling ◽

Hypervalent Iodine ◽

Direct Transformation ◽

Metal Free

A direct transformation of N-aryl formamides to the corresponding phenylurea derivatives via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine reagents as external oxidants.

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