Regioselective Gold-catalyzed Oxidative C-N Bond Formation

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2014 Dec 25

PMID 25539392

Citations 8

Authors

Louis Marchetti

Abhishek Kantak

Riley Davis

Brenton DeBoef

Affiliations

Soon will be listed here.

Abstract

A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.

Citing Articles

Direct C-H amination reactions of arenes with -hydroxyphthalimides catalyzed by cuprous bromide.

Zhang D, Lv B, Gao P, Jia X, Yuan Y Beilstein J Org Chem. 2022; 18:647-652.

PMID: 35706994 PMC: 9174840. DOI: 10.3762/bjoc.18.65.

C-C Cross-Couplings from a Cyclometalated Au(III) C N Complex: Mechanistic Insights and Synthetic Developments.

Bonsignore R, Thomas S, Rigoulet M, Jandl C, Pothig A, Bourissou D Chemistry. 2021; 27(57):14322-14334.

PMID: 34310783 PMC: 8597034. DOI: 10.1002/chem.202102668.

Homogeneous Gold-Catalyzed Oxidation Reactions.

Zheng Z, Ma X, Cheng X, Zhao K, Gutman K, Li T Chem Rev. 2021; 121(14):8979-9038.

PMID: 33591722 PMC: 8623385. DOI: 10.1021/acs.chemrev.0c00774.

Connecting remote C-H bond functionalization and decarboxylative coupling using simple amines.

de Azambuja F, Yang M, Feoktistova T, Selvaraju M, Brueckner A, Grove M Nat Chem. 2020; 12(5):489-496.

PMID: 32152476 PMC: 7192790. DOI: 10.1038/s41557-020-0428-1.

Radical-mediated direct C-H amination of arenes with secondary amines.

Cosgrove S, Plane J, Marsden S Chem Sci. 2018; 9(32):6647-6652.

PMID: 30310597 PMC: 6115623. DOI: 10.1039/c8sc01747f.

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