TY - JOUR
T1 - Fischer Carbene Complexes
T2 - A Glance at Two Decades of Research on Higher-Order Cycloaddition Reactions
AU - Feliciano, Alberto
AU - Vázquez, Juan L.
AU - Benítez-Puebla, Luis J.
AU - Velazco-Cabral, Iván
AU - Cruz Cruz, David
AU - Delgado, Francisco
AU - Vázquez, Miguel A.
N1 - Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2021/6/4
Y1 - 2021/6/4
N2 - 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.
AB - 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.
KW - Fischer carbene complexes
KW - Higher-order cycloaddition
KW - medium-sized cyclic compounds
KW - metal-mediated cycloadditions
KW - transition metals
UR - http://www.scopus.com/inward/record.url?scp=85105918290&partnerID=8YFLogxK
U2 - 10.1002/chem.202005434
DO - 10.1002/chem.202005434
M3 - Artículo de revisión
C2 - 33871119
AN - SCOPUS:85105918290
SN - 0947-6539
VL - 27
SP - 8233
EP - 8251
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 32
ER -