Palladium-catalyzed Aerobic Oxidative Cyclization of N-aryl Imines: Indole Synthesis from Anilines and Ketones

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2012 May 23

PMID 22612535

Citations 24

Authors

Ye Wei

Indubhusan Deb

Naohiko Yoshikai

Affiliations

Soon will be listed here.

Abstract

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

Citing Articles

Synthesis of indoles, indolines, and carbazoles palladium-catalyzed C─H activation.

Rago A, Dong G Green Synth Catal. 2022; 2(2):216-227.

PMID: 36267892 PMC: 9581343. DOI: 10.1016/j.gresc.2021.02.001.

Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions.

Chen X, Bian Y, Mo B, Sun P, Chen C, Peng J RSC Adv. 2022; 10(42):24830-24839.

PMID: 35517475 PMC: 9055228. DOI: 10.1039/d0ra04592f.

Rhodium-Catalyzed Oxidative Annulation of 2- or 7-Arylindoles with Alkenes/Alkynes Using Molecular Oxygen as the Sole Oxidant Enabled by Quaternary Ammonium Salt.

Zhuang W, Zhang J, Zheng Y, Huang Q Molecules. 2021; 26(17).

PMID: 34500762 PMC: 8433977. DOI: 10.3390/molecules26175329.

Regioselective Mercury(I)/Palladium(II)-Catalyzed Single-Step Approach for the Synthesis of Imines and 2-Substituted Indoles.

Gutierrez R, Hernandez-Montes M, Mendieta-Moctezuma A, Delgado F, Tamariz J Molecules. 2021; 26(13).

PMID: 34279432 PMC: 8271454. DOI: 10.3390/molecules26134092.

The role of hypervalent iodine(iii) reagents in promoting alkoxylation of unactivated C(sp)-H bonds catalyzed by palladium(ii) complexes.

Abdolalian P, Tizhoush S, Farshadfar K, Ariafard A Chem Sci. 2021; 12(20):7185-7195.

PMID: 34123345 PMC: 8153247. DOI: 10.1039/d1sc01230d.