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Fischer Carbene Complexes: A Glance at Two Decades of Research on Higher‐Order Cycloaddition Reactions
Author(s) -
Feliciano Alberto,
Vázquez Juan L.,
BenítezPuebla Luis J.,
VelazcoCabral Iván,
Cruz Cruz David,
Delgado Francisco,
Vázquez Miguel A.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005434
Subject(s) - pericyclic reaction , cycloaddition , carbene , chemistry , substituent , reagent , catalysis , computational chemistry , organic reaction , combinatorial chemistry , organic chemistry
The structure of Fischer carbene complexes (FCCs) is electron deficient. If bearing an α,β‐unsaturated system, it can generate a wide variety of compounds by undergoing many different transformations, including higher‐order cycloadditions. The latter are described as pericyclic reactions in which more than six electrons participate. These reactions have been employed in various areas of organic synthesis, resulting in highly selective compounds with a broad range of scaffolds. The first studies on higher‐order cycloadditions involving FCCs frequently yielded competing byproducts. Many groups have attempted to increase selectivity by exploring distinct reaction conditions, reagents and co‐catalysts (e. g., metal‐mediated cycloadditions). The present review is the first to focus exclusively on using higher‐order cycloadditions involving FCCs to synthesize carbocycles and heterocycles. Based on two decades of reports, an analysis is made of the main aspects of the mechanisms proposed for higher‐order cycloadditions and the structural diversity obtained by the substituent effect.