Metal-Free Oxidative Coupling Reactions via σ-Iodonium Intermediates: The Efficient Synthesis of Bithiophenes Using Hypervalent Iodine Reagents

2011 ◽  
Vol 2011 (31) ◽  
pp. 6326-6334 ◽  
Author(s):  
Koji Morimoto ◽  
Tomofumi Nakae ◽  
Nobutaka Yamaoka ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Oxidative Coupling ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Metal Free ◽  
Oxidative Coupling Reactions

Formation of Carbon-Nitrogen Bond Mediated by Hypervalent Iodine Re-agents Under Metal-free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Yaxin O Yang ◽  
Xi Wang ◽  
Jiaxi Xiao ◽  
Yadong Li ◽  
Fengxia Sun ◽  
...  
Keyword(s):  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Metal Free ◽  
Bond Forming ◽  
The Past ◽  
Oxidative Coupling Reactions ◽  
Nitrogen Bond

: In the past several decades, hypervalent iodine chemistry has witnessed prosperous development as hypervalent iodine reagents have been widely used in various organic transformations. Specifically, hypervalent iodine reagents have been vastly used in various bond-forming reactions. Among these oxidative coupling reactions, the reactions involving the formation of C-N bond have been extensively explored to construct various heterocyclic skeletons and synthesize various useful building blocks. This review article is to summarize all the transformations in which carbon-nitrogen bond formation occurred by using hypervalent iodine reagents under metal-free conditions.

scholarly journals Oxidative Coupling of N-Methoxyamides and Related Compounds toward Aromatic Hydrocarbons by Designer μ-Oxo Hypervalent Iodine Catalyst

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1185-1195 ◽  
Author(s):  
Toshifumi Dohi ◽  
Hirotaka Sasa ◽  
Mio Dochi ◽  
Chihiro Yasui ◽  
Yasuyuki Kita
Keyword(s):  
Aromatic Hydrocarbons ◽  
Oxidative Coupling ◽  
Synthetic Methods ◽  
Hypervalent Iodine ◽  
Catalyst Loading ◽  
Coupling Reactions ◽  
Chemical Transformations ◽  
Continuous Development ◽  
Oxidative Coupling Reactions ◽  
Related Compounds

Oxidative coupling strategies that can directly convert the C–H group for chemical transformations are, in theory, ideal synthetic methods to reduce the number of synthetic steps and byproduct generation. Hypervalent iodine reagents have now become one of the most promising tools in developing oxidative couplings due to their unique reactivities that are replacing metal oxidants. As part of our continuous development of oxidative coupling reactions, we describe in this report highly efficient μ-oxo hypervalent iodine catalysts for the direct oxidative coupling of N-methoxyamides and related compounds with aromatic hydrocarbons. The excellent TONs, up to over 100 times, with a best catalyst loading of 0.5 mol% were determined for the oxidative C–H/N–H coupling method, which can provide the most straightforward route to obtaining these unique arylamide compounds.

Highly efficient synthesis of azos catalyzed by the common metal copper (0) through oxidative coupling reactions

RSC Advances ◽  
2014 ◽  
Vol 4 (32) ◽  
pp. 16607 ◽  
Author(s):  
Jiaqing Wang ◽  
Jing He ◽  
Cong Zhi ◽  
Bin Luo ◽  
Xinming Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Highly Efficient ◽  
The Common ◽  
Oxidative Coupling Reactions

Efficient Synthesis of Several Natural Oligostilbenes from the ­Biomimetic Oxidation of Brominated Isorhapontigenin

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1825-1831 ◽  
Author(s):  
Xingchao Guan ◽  
Meijie Liu ◽  
Zhibo Shao ◽  
Hongpeng Li ◽  
Lu Ran ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Biomimetic Oxidation ◽  
Solvent Systems ◽  
First Time ◽  
Oxidative Coupling Reactions

This study extensively investigated the regioselective oxidative coupling reactions of 5-bromoisorhapontigenin catalyzed by ­FeCl3·6H2O or HRP/H2O2 in different solvent systems and the distinct reductive debromination of the isolated dimeric coupling intermediates. Natural (±)-bisisorhapontigenin A and (±)-lehmbachol A and B were efficiently prepared. (±)-Gnetuhainin I, (±)-gnemontanin E, (±)-7-O-ethylgnetuhainin I, and (±)-gnemontanin F were synthesized for the first time.

scholarly journals An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1527
Author(s):  
Saiwen Liu ◽  
Ru Chen ◽  
Guowen He ◽  
Jin Zhang
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Coupling Reagents ◽  
Oxidative Esterification ◽  
Metal Free ◽  
High Yields ◽  
Oxidative Coupling Reactions

An esterification and amination of benzylic C–H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidative coupling reactions with various diarylmethanes. A close to equal amount of coupling reagents was enough to afford the product in good to high yields.

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