Diversity-Oriented Synthesis of Polycyclic Diazinic Scaffolds

Gigant, Nicolas; Claveau, Elise; Bouyssou, Pascal; Gillaizeau, Isabelle

doi:10.1021/ol203364b

Cited by 25 publications

(6 citation statements)

References 28 publications

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“…BDT cation synthesis reactions were adapted from literature reports [54] and are described in detail in Scheme S1 for BDT‐C2 and Scheme S2 for BDT‐C4 and BDT‐C6. [55] Characterizations of the final cations and reaction intermediates by 1 H NMR spectroscopy are given in Figures S19 and S20, for BDT‐C2, in Figures S21 and S22 for BDT‐C4, and finally in Figures S23 and S24 for BDT‐C6.…”

Section: Methodsmentioning

confidence: 99%

Benzodithiophene‐Based Spacers for Layered and Quasi‐Layered Lead Halide Perovskite Solar Cells

et al. 2021

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Incorporating extended pi-conjugated organic cations in layered lead halide perovskites is a recent trend promising to merge the fields of organic semiconductors and lead halide perovskites. Herein, we integrate benzodithiophene (BDT) into Ruddlesden-Popper (RP) layered and quasi-layered lead iodide thin films (with methylammonium, MA) of the form (BDT) 2 MA nÀ 1 Pb n I 3n + 1 . The importance of tuning the ligand chemical structure is shown as an alkyl chain length of at least six carbon atoms is required to form a photoactive RP (n = 1) phase. With N = 20 or 100, as prepared in the precursor solution following the formula (BDT) 2 MA NÀ 1 Pb N I 3N + 1 , the performance and stability of devices surpassed those with phenylethylammonium (PEA). For N = 100, the BDT cation gave a power conversion efficiency of up to 14.7 % vs. 13.7 % with PEA. Transient photocurrent, UV photoelectron spectroscopy, and Fourier transform infrared spectroscopy point to improved charge transport in the device active layer and additional electronic states close to the valence band, suggesting the formation of a Lewis adduct between the BDT and surface iodide vacancies.

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Section: Methodsmentioning

confidence: 99%

Benzodithiophene‐Based Spacers for Layered and Quasi‐Layered Lead Halide Perovskite Solar Cells

et al. 2021

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“…Additional references cited within the Supporting Information. [60][61][62][63][64][65][66][67][68][69][70] Author Contributions…”

Section: Supporting Informationmentioning

confidence: 99%

Multicomponent and Metal‐Free Diels–Alder/Aromatization Approach to the Stereospecific Synthesis of E‐(Hetero)Stilbenes and Diarylacetylenes

Ballarotto,

Cerra,

Temperini

2023

Eur J Org Chem

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Herein, we present a novel and metal‐free approach to the stereospecific synthesis of E‐stilbenes. Starting from substituted 6‐arylhexa‐3,5‐dien‐2‐ones, a multicomponent enolacetylation/intermolecular Diels–Alder reaction was performed using ethyl acetate as a green solvent. The obtained cycloadducts were then oxidized without purification to produce the stilbenic products in good yields up to 67 % and with complete (E)‐stereospecificity and regioselectivity. Moreover, heterostilbenes were synthetized using this approach, displaying the potential applications of this protocol in pharmaceutical and material sciences. The proposed methodology was further extended to the synthesis of diarylacetylenes, furnishing a new metal‐free synthetic access to this important class of compounds. Furthermore, DFT calculations were performed confirming a concerted [4+2] reaction mechanism of the key ring‐forming step. At last, the energetic analysis of the possible transition states helps to shed some light on the experimentally observed total regio‐ and chemoselectivity.

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“…The corresponding 4‑substituted 3-azabicyclo[3.1.0]-hexan-2-ones 16 – 23 were obtained with high diastereoselectivity (dr > 95:5), due to hydride transfer on the less congested face of the N ‑acyliminium ion, and were isolated in excellent yields (90–97%) (Table , entries 1–8). It is noteworthy that no competing Pictet–Spengler cyclization was observed for the N ‑acyliminium ions generated from enamides 7 – 12 since this would require the formation of a five-membered ring which is disfavored (5- endo -trig process). − Formation of a seven-membered ring by competitive Pictet–Spengler cyclization was also not observed as a side reaction in the case of enamides 13 and 14 . , By contrast for enamide 15 , derived from homoveratrylamine, the intermolecular reduction can compete with the Pictet–Spengler cyclization which leads to the formation of a six-membered ring. Thus, under the previously developed conditions, a mixture of pyrrolidone 24 and tetracyclic compound 25 was obtained in a 20:80 ratio.…”

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confidence: 99%

A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides

et al. 2013

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Diversity-Oriented Synthesis of Polycyclic Diazinic Scaffolds

Abstract: An efficient and versatile synthesis of a polycyclic diazinic system starting from oxazine has been developed using a two-step Michael/retro Michael and cyclization sequence. The substrates were synthesized with good to high yields giving rapid access to molecular diversity.

Cited by 25 publications

References 28 publications

Benzodithiophene‐Based Spacers for Layered and Quasi‐Layered Lead Halide Perovskite Solar Cells

Benzodithiophene‐Based Spacers for Layered and Quasi‐Layered Lead Halide Perovskite Solar Cells

Multicomponent and Metal‐Free Diels–Alder/Aromatization Approach to the Stereospecific Synthesis of E‐(Hetero)Stilbenes and Diarylacetylenes

A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides

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