The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2016

Herndon, James W.

doi:10.1016/j.ccr.2017.09.003

Cited by 15 publications

(2 citation statements)

References 1,285 publications

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“…Imines are important building blocks because they can contain not only nucleophilic or electrophilic sites but also a combination of the two, thus allowing for different reaction pathways in some cases [15][16][17]. Usually, this reactivity favours the synthesis of cyclic compounds in a few steps [15,16,[18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Reactivity of a Fischer Alkynyl Carbene Complex with Benzylidene Anilines

Delgado Reyes,

Feliciano,

Vazquez

et al. 2024

J. Mex. Chem. Soc.

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The reaction between the Fischer carbene complex (CO)5Cr=C(OEt)CºCPh and various benzylidene anilines RCH=NR1 was promoted by microwave irradiation, generating stable cross-conjugated metallahexatrienes in 45-70 % yield. Compared to conventional heating, the present conditions provided shorter reaction times with moderate yields. The geometrical configuration and the most stable conformation for each of the Fischer carbene complexes and their oxidation products were established by NMR and DFT analysis. The reaction mechanism was explored by DFT calculations of the potential energy surface, suggesting a 1,4-addition/ring closure/electrocyclic opening cascade process. Resumen. Se reporta la reactividad entre el carbeno de Fischer (CO)5Cr=C(OEt)CºCPh y las bencilidén anilinas, RCH=NR1, empleando irradiación de microondas. Los resultados indican que el calentamiento por microondas generó metalohexatrienos cruzados estables en rendimientos de 45-70 %, mostrando además, que los nuevos complejos se obtienen en tiempos de reacción más cortos y rendimientos moderados en comparación con las condiciones de calentamiento convencional. La configuración geométrica y la conformación más estable para los complejos carbénicos de Fischer y de sus derivados oxidados fueron establecidos por medio de RMN y DFT. La exploración de la superficie de energía potencial por cálculos DFT mostró que el proceso consistió en una reacción en cascada incluyendo una secuencia de adición-1,4, cierre de anillo y apertura electrocíclica.

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Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Reactivity of a Fischer Alkynyl Carbene Complex with Benzylidene Anilines

Delgado Reyes,

Feliciano,

Vazquez

et al. 2024

J. Mex. Chem. Soc.

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“…ompounds with transition metal-carbon triple bonds, namely metal carbyne complexes, have attracted much interest and attention since the seminal work by Fischer et al [1][2][3] . The M≡C bonds have been shown rich reactivity with electrophiles and nucleophiles [4][5][6][7][8] . Therefore, metal carbyne complexes are valuable in synthetic chemistry as precursors for interesting organometallic compounds [9][10][11] , and can be used as homogeneous catalysts in the synthesis of organic compounds and polymers [12][13][14][15][16][17][18] .…”

mentioning

confidence: 99%

Addition of alkynes and osmium carbynes towards functionalized dπ–pπ conjugated systems

et al. 2020

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The metal-carbon triple bonds and carbon-carbon triple bonds are both highly unsaturated bonds. As a result, their reactions tend to afford cycloaddition intermediates or products. Herein, we report a reaction of M≡C and C≡C bonds that affords acyclic addition products. These newly discovered reactions are highly efficient, regio- and stereospecific, with good functional group tolerance, and are robust under air at room temperature. The isotope labeling NMR experiments and theoretical calculations reveal the reaction mechanism. Employing these reactions, functionalized dπ-pπ conjugated systems can be easily constructed and modified. The resulting dπ-pπ conjugated systems were found to be good electron transport layer materials in organic solar cells, with power conversion efficiency up to 16.28% based on the PM6: Y6 non-fullerene system. This work provides a facile, efficient methodology for the preparation of dπ-pπ conjugated systems for use in functional materials.

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Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

et al. 2018

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2016

Cited by 15 publications

References 1,285 publications

Microwave-Assisted Reactivity of a Fischer Alkynyl Carbene Complex with Benzylidene Anilines

Microwave-Assisted Reactivity of a Fischer Alkynyl Carbene Complex with Benzylidene Anilines

Addition of alkynes and osmium carbynes towards functionalized dπ–pπ conjugated systems

Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

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