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Synthesis 2021; 53(01): 79-94
DOI: 10.1055/s-0040-1707272
DOI: 10.1055/s-0040-1707272
short review
The Power of Iron Catalysis in Diazo Chemistry
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) Discovery Grant RGPIN-2017-04272, the Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT) (Centre in Green Chemistry and Catalysis) Strategic Cluster FRQNT-2020-RS4-265155-CCVC, and Université Laval.
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
Publication History
Received: 27 June 2020
Accepted after revision: 04 August 2020
Article published online:
15 September 2020
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