Synthesis of 4,6-disubstituted 2-(4-morpholinyl)pyrimidines by cross-coupling reactions using triorganoindium compounds

Martı́nez, M. Montserrat; Pérez-Caaveiro, Cristina; Peña‐López, Miguel; Sarandeses, Luis A.; Sestelo, José Pérez

doi:10.1039/c2ob26398j

Cited by 12 publications

(4 citation statements)

References 35 publications

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“…The O6PMe emission displays two clearly distinguishable peaks at 600 and 650 nm and is blueshifted with respect to O5PMe.The broad nature of O5PMe emission beyond 650 nm is suggestive of H-aggregated stacking, improved intermolecular interactions, and the presence of multiple emissive species. 47,48 We also see that while the absorption spectra of O6PMe in solution state (Figure S14) are comparable to its solid-state spectra, the O5PMe solid-state spectra are hypsochromically shifted with respect to its solution-state spectra, further indicative of Haggregated stacking in O5PMe films.…”

Section: ■ Results and Discussionmentioning

confidence: 75%

Singlet Fission in Pechmann Dyes: Planar Chromophore Design and Understanding

Girija,

Zeng,

Myers

et al. 2024

J. Am. Chem. Soc.

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Singlet fission in organic chromophores holds the potential for enhancing photovoltaic efficiencies beyond the singlejunction limit. The most basic requirement of a singlet fission material is that it has a large energy gap between its first singlet and triplet excited states. Identifying such compounds is not simple and has been accomplished either through computational screening or by subtle modifications of previously known fission materials. Here, we propose an approach that leverages ground and excited-state aromaticity combined with double-bond conformation to establish simple qualitative design rules for predicting fundamental optical properties without the need for computational modeling. By investigating two Pechmann dye isomers, we demonstrate that although their planarity and degree of charge transfer are similar, singlet fission is active in the isomer with a trans-conformation, while the cisisomer exhibits greater favorability for polaronic processes, experimentally validated using ultrafast and electron spin resonance spectroscopy. Our results offer a new design perspective that provides a rational framework for tailoring optoelectronic systems to specific applications such as singlet fission or triplet−triplet annihilation

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Section: ■ Results and Discussionmentioning

confidence: 75%

Singlet Fission in Pechmann Dyes: Planar Chromophore Design and Understanding

Girija,

Zeng,

Myers

et al. 2024

J. Am. Chem. Soc.

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“…In recent years we have shown that indium organometallics are useful reagents in metal-catalyzed cross-coupling reactions. , Besides their high efficiency, versatility, and selectivity in cross-coupling reactions, triorganoindium reagents (R 3 In) are particularly effective for the synthesis of functionalized heterocyclic compounds, and they exhibit high selectivity in coupling reactions with 3,4-dihalomaleimides, 2,5-dibromothiophenes, and 4,6-dichloropyrimidines . As a continuation of our studies into the application of R 3 In in organic synthesis, we report herein an efficient approach to trisubstituted imidazoles by selective and sequential palladium-catalyzed cross-coupling reactions of triorganoindium reagents with 2,4,5-trihaloimidazoles and the application of this approach to the synthesis of neurodazine and analogues.…”

Section: Introductionmentioning

confidence: 79%

“…Triorganoindium compounds were prepared according to previously published methods − by treatment of the corresponding organolithium reagents (3 equiv., ∼0.5 M in dry THF) with a solution of InCl 3 (1.1 equiv., ∼0.05 M in dry THF) at −78 or −20 °C and warming to room temperature.…”

Section: Experimental Sectionmentioning

confidence: 99%

Triorganoindium Reagents in Selective Palladium-Catalyzed Cross-Coupling with Iodoimidazoles: Synthesis of Neurodazine

et al. 2014

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Triorganoindium reagents (R3In, R = aryl, heteroaryl, alkynyl) react selectively under palladium catalysis with N-benzyl-2,4,5-triiodoimidazole to afford the C-2 monocoupling products. The reaction proceeds efficiently for a variety of aryl- and heteroarylindium reagents with the transfer of all three organic groups attached to the metal. The coupling products can be used in a subsequent two-fold cross-coupling to give trisubstituted imidazoles in good yields. This approach was employed to synthesize neurodazine and analogues in good yields.

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“…dibrominated pyridine, 117 . Triarylindium reagents were also used to synthesize C4 → C6 diaryl pyrimidines, 122 via Pd(PPh 3 ) 4 -catalyzed sequential arylation of 121 . One-pot arylation provided an unsymmetrical diaryl product in yields that were comparable with that of product formed in the stepwise route, 122a .…”

Section: Sequential C-arylation Of 6-membered Heteroarenesmentioning

confidence: 99%

Strategic Advances in Sequential C-Arylations of Heteroarenes

et al. 2020

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Sequence-specific C-arylation strategies have important applications in medicinal and material research. These strategies allow C–C bond formations in a regioselective manner to synthesize large molecular libraries for studying structure–activity profiles. The past decade has seen the development of single C–C bond forming reactions using various transition-metal catalysts, cryogenic metalation strategies, and metal-free methods. Sequential arylations of heterocycles allow for the formation of multiaryl derivatives and are a preferred choice over de novo synthetic routes. This perspective sheds light on recent strategic advances to develop various sequential synthetic routes for the multiarylation of heteroarenes. This perspective addresses many challenges in optimizing sequential routes with respect to catalysts, reaction parameters, and various strategies adopted to obtain diversely arylated products.

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Synthesis of 4,6-disubstituted 2-(4-morpholinyl)pyrimidines by cross-coupling reactions using triorganoindium compounds

Cited by 12 publications

References 35 publications

Singlet Fission in Pechmann Dyes: Planar Chromophore Design and Understanding

Singlet Fission in Pechmann Dyes: Planar Chromophore Design and Understanding

Triorganoindium Reagents in Selective Palladium-Catalyzed Cross-Coupling with Iodoimidazoles: Synthesis of Neurodazine

Strategic Advances in Sequential C-Arylations of Heteroarenes

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