The Power of Iron Catalysis in Diazo Chemistry

Abstract

The use of iron catalysis to enable reactions with diazo compounds has emerged as a valuable tool to forge carbon-carbon or carbon-heteroatom bonds. While diazo compounds are often encountered with toxic and expensive metal catalysts, such as Rh, Ru, Pd, Ir, and Cu, a resurgence of Fe catalysis has been observed. This short review will showcase and highlight the recent advances in iron-mediated reactions of diazo compounds. 1 Introduction 2 Insertion Reactions 2.1 Insertion into B-H Bonds 2.2 Insertion into Si-H Bonds 2.3 Insertion into N-H Bonds 2.4 Insertion into S-H bonds 3 Ylide Formation and Subsequent Reactions 3.1 Doyle-Kirmse Rearrangement 3.2 [1,2]-Stevens and Sommelet-Hauser Rearrangements 3.3 Olefination Reactions 3.4 Cycloaddition Reactions 3.5 gem -Difluoroalkenylation 4 Three-Component Reactions 5 Miscellaneous 6 Conclusion.