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Regioselective C-H Bond Amination by Aminoiodanes

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Specialty Chemistry
Date 2015 Jan 31
PMID 25632832
Citations 1
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Abstract

A new approach for the direct amination of 2-phenylpyridine derivatives using a diphthalimide-iodane and copper triflate has been developed. A series of different 2-phenylpyridine derivatives were aminated with yields up to 88%. Mechanistic investigations indicate that the reaction proceeds via a copper-mediated single electron transfer.

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A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

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PMID: 30033454 PMC: 6113863. DOI: 10.1039/c8cs00201k.

References
1.
Whitfield S, Sanford M . Reactivity of Pd(II) complexes with electrophilic chlorinating reagents: isolation of Pd(IV) products and observation of C-Cl bond-forming reductive elimination. J Am Chem Soc. 2007; 129(49):15142-3. DOI: 10.1021/ja077866q. View

2.
John A, Nicholas K . Copper-catalyzed amidation of 2-phenylpyridine with oxygen as the terminal oxidant. J Org Chem. 2011; 76(10):4158-62. DOI: 10.1021/jo200409h. View

3.
Sun K, Li Y, Xiong T, Zhang J, Zhang Q . Palladium-catalyzed C-H aminations of anilides with N-fluorobenzenesulfonimide. J Am Chem Soc. 2011; 133(6):1694-7. DOI: 10.1021/ja1101695. View

4.
Alberico D, Scott M, Lautens M . Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem Rev. 2007; 107(1):174-238. DOI: 10.1021/cr0509760. View

5.
Tsang W, Zheng N, Buchwald S . Combined C-H functionalization/C-N bond formation route to carbazoles. J Am Chem Soc. 2005; 127(42):14560-1. DOI: 10.1021/ja055353i. View