Condensation-Based Methods for the C–H Bond Functionalization of Amines

Abstract

This review aims to provide a comprehensive overview of condensation-based methods for the C–H bond functionalization of amines that feature azomethine ylides as key intermediates. These transformations are typically redox-neutral and share common attributes with classic name reactions such as the Strecker, Mannich, ­Friedel–Crafts, Pictet–Spengler, and Kabachnik–Fields reactions, while incorporating a redox-isomerization step. This approach provides an ideal platform to rapidly transform simple starting materials into complex amines.

1 Introduction

1.1 General Remarks

1.2 Overview

1.3 Scope of This Review

2 Aromatization of Cyclic Amines

2.1 Pyridines from Piperidine

2.2 Isoquinolines from Tetrahydroisoquinolines and Quinolines from Tetrahydroquinolines

2.3 Pyrroles from 3-Pyrroline or Pyrrolidine

2.4 Indoles from Indolines

3 Pericyclic Reactions

3.1 (3+2)-Dipolar Cycloadditions

3.2 6π-Electrocyclizations

3.3 1,5-Proton Shifts

4 Redox-Variants of Classic Transformations Incorporating a C–H Bond Functionalization Step

4.1 α-Cyanation

4.2 α-Alkynylation

4.3 α-Phosphonation

4.4 α-Arylation

4.5 α-Alkylation with Ketones

4.6 Redox-Ugi Reaction

4.7 Miscellaneous Intermolecular Reactions

5 Redox-Annulations

6 Reactions Involving β-C–H Bond Functionalization

7 Outlook

Key words

C–H bond functionalization - amines - heterocycles - redox-neutral - redox-isomerization - condensation

Publication History

Received: 08 July 2021

Accepted after revision: 02 September 2021

Accepted Manuscript online:
02 September 2021

Article published online:
12 October 2021

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