Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling

2016 ◽  
Vol 14 (38) ◽  
pp. 8947-8951 ◽  
Author(s):  
Koji Morimoto ◽  
Yusuke Ohnishi ◽  
Daichi Koseki ◽  
Akira Nakamura ◽  
Toshifumi Dohi ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Iodonium Salts ◽  
Metal Free

We have developed a direct oxidative C–H bond arylation of pyrroles with various aromatic compounds via stabilized pyrrolyl iodonium(iii) salts generated from modified hypervalent iodine(iii) and TMSCl as an activator.

Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1680-1694 ◽  
Author(s):  
Koji Morimoto ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Aromatic Compounds ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Heteroaromatic Compounds ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Biaryl Coupling

The biaryl unit containing a heteroatom is a key structure in a large number of natural products and π-conjugated organic systems. The cross-couplings can provide powerful methods for the construction of biaryls and heterobiaryls; thus the development of a new coupling method has been intensively studied by synthetic chemists. Therefore, the oxidative biaryl coupling reaction of arenes containing a heteroatom is a significantly attractive, convenient, and straightforward route to the synthesis of biaryls due to its operational simplicity avoiding the preparation of the corresponding halogenated and metallated arenes. In this report, recent progress in the field of metal-free oxidative cross-coupling reactions of aromatic compounds using hypervalent iodine(III) reagents, is presented.1 Introduction2 Cyanation and Halogenation Reactions of Heteroaromatic Compounds3 Biaryl Coupling Reaction of Heteroaromatic Compounds3.1 Regioselective Coupling Reaction of Thiophenes3.2 Cross-Coupling Reaction of Thiophenes3.3 Coupling Reaction of EDOT and Pyrroles3.4 Cross-Coupling Reaction of Pyrroles4 Cross-Coupling Reaction of Anilines5 Cross-Coupling Reaction of Phenols6 Cross-Coupling Reaction of N-Heteroaromatics with Aryl Radicals from Diaryliodonium(III) Salts7 Conclusion

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

2015 ◽  
Vol 39 (2) ◽  
pp. 805-809 ◽  
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.

ChemInform Abstract: Clean Synthesis of N-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent.

ChemInform ◽  
2016 ◽  
Vol 47 (6) ◽  
pp. no-no
Author(s):  
Koji Morimoto ◽  
Ryosuke Ogawa ◽  
Daichi Koseki ◽  
Yusuke Takahashi ◽  
Toshifumi Dohi ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Clean Synthesis

Metal-Free Oxidative Cross-Coupling of Pyrroles with Electron-Rich Arenes Using Recyclable Hypervalent Iodine(III) Reagent

Heterocycles ◽  
2018 ◽  
Vol 97 (1) ◽  
pp. 632
Author(s):  
Yasuyuki Kita ◽  
Koji Morimoto ◽  
Toru Kamitanaka ◽  
Toshifumi Dohi
Keyword(s):  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Metal Free

ChemInform Abstract: Metal-Free Oxidative Cross-Coupling of Unfunctionalized Aromatic Compounds.

ChemInform ◽  
2009 ◽  
Vol 40 (25) ◽  
Author(s):  
Yasuyuki Kita ◽  
Koji Morimoto ◽  
Motoki Ito ◽  
Chieko Ogawa ◽  
Akihiro Goto ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Cross Coupling ◽  
Metal Free

Metal-Free Oxidative Cross-Coupling Reaction of Thiophene Iodonium Salts with Pyrroles

2016 ◽  
Vol 2016 (25) ◽  
pp. 4294-4297 ◽  
Author(s):  
Koji Morimoto ◽  
Akira Nakamura ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Iodonium Salts ◽  
Metal Free ◽  
Cross Coupling Reaction

scholarly journals Clean Synthesis of N-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent

2015 ◽  
Vol 63 (10) ◽  
pp. 819-824 ◽  
Author(s):  
Koji Morimoto ◽  
Ryosuke Ogawa ◽  
Daichi Koseki ◽  
Yusuke Takahashi ◽  
Toshifumi Dohi ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Clean Synthesis

ChemInform Abstract: Metal-Free Oxidative Cross-Coupling Reaction of Thiophene Iodonium Salts with Pyrroles.

ChemInform ◽  
2016 ◽  
Vol 47 (52) ◽  
Author(s):  
Koji Morimoto ◽  
Akira Nakamura ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Iodonium Salts ◽  
Metal Free ◽  
Cross Coupling Reaction
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