Iron-catalyzed Benzannulation Reactions of 2 ‑ Alkylbenzaldehydes and Alkynes Leading to...
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Transcript of Iron-catalyzed Benzannulation Reactions of 2 ‑ Alkylbenzaldehydes and Alkynes Leading to...
![Page 1: Iron-catalyzed Benzannulation Reactions of 2 ‑ Alkylbenzaldehydes and Alkynes Leading to Naphthalene Derivatives An efficient and practical method for.](https://reader033.fdocuments.in/reader033/viewer/2022051216/5665b4901a28abb57c923430/html5/thumbnails/1.jpg)
Iron-catalyzed Benzannulation Reactionsof 2‑Alkylbenzaldehydes and AlkynesLeading to Naphthalene Derivatives
An efficient and practical method for the synthesis of naphthalene derivatives via Fe(III)-catalyzed benzannulation of 2-(2-oxoethyl)-benzaldehydes
and alkynes has been developed. The system holds the advantages of cheap catalysts, wide substrate scope, and mild reaction conditions.
S. Zhu y col. Org. Lett. (South China University of Technology, Guangzhou))
5% mol1-2 h, 60 ºC
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Trabajo previo
Este trabajo
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R
R
R
Catalizadores: AgSbF6, ZnCl2, FeCl3
No reacción sin catalizador o con catálisis ácida (H+)
H,OMe, F, CF3 H, Ph, Alquilo, Br
XC6H4, Alquilo
60-99%X: MeO, Me, Cl, H,(CF3)2
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Mecanismo propuesto
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N
O
RO
R1
R3
R4
N
OR
OH
R1
O
N
R3
R4
R
OH
R1
N
R3
R4
R1
N
O
RO
R1
R3
R4
N
OR
OH
R1
O
NR
3
R4
R
OH
R1
N
R3
R4
R1
N
O
RO
R1
R3
R4
N
OR
OH
R1
N
O
R3
R4
R
OH
R1
N
R3
R4
R1
Fe3+
Fe3+
Fe3+
+ ++ +
¿Síntesis de heterociclos?
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Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation
F. Mo, J. Wang y col. J. Org. Chem. (Beijing National Laboratory of Molecular Sciences)
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Rutas a ácidos arilborónicos y arilboronatos
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Comparación con otros métodos
- Ausencia de metal- Arilaminas abundantes y no caras- Tolerancia de grupos funcionales- Condiciones suaves
BPO
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Productos aromáticos
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Boración-acoplamiento C-C secuenciales
Het-Bpin inestable en gel de sílice
Escalable a cantidades de multigramo
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Mecanismo propuesto
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Synthesis of Imidazo[1,2-a]pyridines: “Water-Mediated” Hydroamination and Silver-Catalyzed Aminooxygenation
S. Adimurthy y col. J. Org. Chem. (Central Salt and Marine Chemicals Research Institute, Gujarat)
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ansiolítico
Fallo cardiaco
Osteoporosis
VIH
ansiolíticosedante
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Hidroaminación
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Deuteración
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Aminooxigenación