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Direct Amination of Aromatic C–H Bonds with Free Amines

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Abstract

Aromatic amines belong to a highly important class of organic compounds which are found in various natural products, functional materials, and pharmaceutical agents. Their prevalence has sparked continuing interest in the development of highly efficient and environmentally benign synthetic strategies for the construction of these compounds. Cross-dehydrogenative coupling reactions between two unmodified C(X)–H bonds have recently emerged as a versatile and powerful strategy for the fabrication of new C(X)–C(X) bonds. In this context, several procedures have been reported for the synthesis of aromatic amines through the direct amination of aromatic C–H bonds with free amines. This review highlights recent advances and progress in this appealing research arena, with special emphasis on the mechanistic features of the reactions.

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Abbreviations

BHT:

2,6-Diisopropyl-4-methylphenol

BODIPY:

Boron-dipyrromethene

C2Cl4 :

Tetrachloroethylene

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DCE:

Dichloroethane

DCM:

Dichloromethane

DDQ:

2,3-Dichloro-5,6-dicyano-p-benzoquinone

DMF:

N,N-Dimethylformamide

DMSO:

Dimethyl sulfoxide

DMPU:

N,N′-dimethylpropyleneurea

DTBMP:

2,6-di-tert-butyl-4-methylpyridine

GVL:

γ-Valerolactone

HFIP:

1,1,1,3,3,3-Hexafluoro-2-propanol

MeCN:

Acetonitrile

NHPI:

N–Hydroxyphthalimide

NIS:

N-Iodosuccinimide

NMP:

N-Methyl-2-pyrrolidone

PIDA:

(Diacetoxy)iodobenzene

TBHP:

tert-Butyl hydroperoxide

TBP:

tert-Butyl peroxide

TEMPO:

2,2,6,6-Tetramethyl-1-piperidinyloxy

THF:

Tetrahydrofuran

T-HYDRO:

70 wt  tBuOOH in H2O

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Authors and Affiliations

  1. School of Forestry, Henan Agricultural University, Zhengzhou, 450002, China

    Yafeng Yang & Dangquan Zhang

  2. Department of Chemistry, Payame Noor University, Tehran, Iran

    Esmail Vessally

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  1. Yafeng Yang
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  2. Dangquan Zhang
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Yang, Y., Zhang, D. & Vessally, E. Direct Amination of Aromatic C–H Bonds with Free Amines. Top Curr Chem (Z) 378, 37 (2020). https://doi.org/10.1007/s41061-020-0300-1

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