Palladium-Catalyzed Synthesis of Heterocyclic Ring Systems by Combination of Regioselective C–C with Twofold C–N Couplings

Abstract

The combination of regioselective palladium-catalyzed C–C with twofold C–N couplings allows for the synthesis of a variety of heterocyclic ring systems. Starting materials include thiophenes and benzothiophenes, pyrroles and indoles, furans and benzofurans, pyridines, quinolines and quinoxalines, complex heterocyclic systems and benzophenone derivatives. The products are in many cases complex polyheterocyclic systems, which are not readily available by other methods or, in a number of cases, were not described in the literature before. They are of pharmacological relevance or interesting in the field of material science. Products include thieno[3,2-b:4,5-b′]diindoles, thieno[3,2-b]indoles, thieno[3,4-b]indoles, 5,10-dihydroindolo[3,2-b]indoles, furo[3,2-b:4,5-b′]diindoles, benzo[4,5]furo[3,2-b]indoles, 5,7-dihydropyrido[3,2-b:5,6-b′]diindoles, 5,7-dihydropyrido[2,3-b:6,5-b´]diindoles, α-, β-, γ- and δ-carbolines, indolo[3,2-b]quinolines, indolo[2,3-b]quinolines, indolo[3,2-c]quinolines, indoloquinoxalines, pyrido[2′,1′:2,3]imidazo[4,5-b]indoles, thiadiazolo[2′,3′:2,3]imidazo[4,5-b]indoles, benzo[b]carbazolediones, acridones and thieno[3,2-b]quinolones.

Contents

1 Introduction

2 Thiophenes and Benzothiophenes

3 Pyrroles and Indoles

4 Furans and Benzofurans

5 Pyridines

6 Quinolines and Quinoxalines

7 Complex Heterocyclic Systems

8 2,3-Dibromonaphthoquinone

9 Benzophenone Derivatives

10 Conclusions

Key words

catalysis - cross-coupling - heterocycles - palladium - regioselectivity

Publication History

Received: 23 February 2022

Accepted after revision: 17 March 2022

Article published online:
25 April 2022

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