Carbon–Carbon Bond Forming Reactions in Diazines via Transition-Metal-Catalyzed C–H Bond Activation

Rafael Gramage-Doria; Christian Bruneau

doi:10.1055/a-2134-0307

Synthesis, Table of Contents

Synthesis 2023; 55(21): 3470-3486
DOI: 10.1055/a-2134-0307

special topic

C–H Bond Functionalization of Heterocycles

Carbon–Carbon Bond Forming Reactions in Diazines via Transition-Metal-Catalyzed C–H Bond Activation

Rafael Gramage-Doria ∗

,

Christian Bruneau

Abstract

All articles of this category

Abstract

An overview of the key achievements concerning C–C bond-forming processes with diazines (pyridazines, pyrimidines, and pyrazines) and benzodiazines (cinnolines, phthalazines, quinazolines, and quinoxalines) under transition-metal-catalyzed C–H activation is presented. The focus is on examples in which C–H functionalization takes place in the diazine or benzodiazine core because of the relevance of these compounds in material science and as active pharmaceutical ingredients. These metal-catalyzed protocols benefit from the biased reactivity of the C–H bonds targeted or from the presence of a rationally designed directing group proximate to the C–H bond to be functionalized. As such, innovative alkylations, alkenylations, alkynylations, arylations, and carboxylations are accomplished within such skeletons in a step- and atom-economy fashion.

1 Introduction

2 Transition-Metal-Catalyzed C–H Alkylation of Diazines

3 Transition-Metal-Catalyzed C–H Alkynylation of Diazines

4 Transition-Metal-Catalyzed C–H Alkenylation of Diazines

5 Transition-Metal-Catalyzed C–H Arylation of Diazines

6 Transition-Metal-Catalyzed C–H Carboxylation of Diazines

7 Conclusion

Key words

diazines - C–H activation - arylation - alkenylation - alkylation - metal catalyst

Full Text

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