Simple preparation of aryltributylstannanes and its application to one-pot synthesis of diaryl ketones

Oikawa, Asuka; Kindaichi, Gan; Shimotori, Yasutaka; Okimoto, Mitsuhiro; Hoshi, Masayuki

doi:10.1016/j.tet.2015.01.048

Cited by 15 publications

(7 citation statements)

References 83 publications

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“…Eluent: CH 2 Cl 2 . The spectroscopic data correspond to the literature . 1 H NMR (300 MHz, CDCl 3 ): δ = 3.95 (s, 6 H), 7.15 (d, J = 8.9 Hz, 4 H), 8.78 (d, J = 8.9 Hz, 4 H) ppm.…”

Section: Methodsmentioning

confidence: 70%

“…General Information: The reagents were purchased from commercial sources and used as received. 5,6‐Dihydro[1,2,5]thiadiazolo[3,4‐ d ]pyridazine‐4,7‐dione ( 3 ) (for details see Supporting Information), [5‐(1,3‐dioxolan‐2‐yl)thiophen‐2‐yl]boronic acid ( 5b ), (9‐hexyl‐9 H ‐carbazol‐3‐yl)boronic acid ( 5d ), [4‐(diphenylamino)phenyl]boronic acid ( 5l ), [4‐( p ‐tolyl)‐1,2,3,3a,4,8b‐hexahydrocyclopenta[ b ]indol‐7‐yl]boronic acid ( 5m ), [5‐(1,3‐dioxolan‐2‐yl)thiophen‐2‐yl]tributylstannane ( 8b ), [2,2′‐bithiophen]‐5‐yltributylstannane ( 8j ), tributyl(thiophen‐3‐yl)stannane ( 8k ), tributyl(4‐methoxyphenyl)stannane ( 8i ), tributyl( p ‐tolyl)stannane ( 8h ) were prepared according to the published methods and characterized by NMR spectra. All synthetic operations were performed under a dry argon atmosphere.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of the 4,7‐Dibromo Derivative of Highly Electron‐Deficient [1,2,5]Thiadiazolo[3,4‐d]pyridazine and Its Cross‐Coupling Reactions

et al. 2018

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An efficient synthesis of 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐d]pyridazine is reported. For the first time, palladium‐catalysed cross‐coupling reactions of a dihalo derivative was found to be a powerful tool for the selective formation of various mono‐ and diarylated derivatives of strongly electron‐accepting heterocycles. Suzuki–Miyaura coupling can be successfully employed for the preparation of mono‐arylated derivatives, whereas Stille coupling is useful for both mono‐ and diaryl(hetaryl)ated heterocycles. The cyclic voltammogram showed that 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐d]pyridazine can be easily oxidized to form a stable anion radical. The calculated values of ELUMO confirmed that [1,2,5]thiadiazolo[3,4‐d]pyridazine is one of the strongest electron–acceptor systems.

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“…Eluent: CH 2 Cl 2 . The spectroscopic data correspond to the literature . 1 H NMR (300 MHz, CDCl 3 ): δ = 3.95 (s, 6 H), 7.15 (d, J = 8.9 Hz, 4 H), 8.78 (d, J = 8.9 Hz, 4 H) ppm.…”

Section: Methodsmentioning

confidence: 70%

Section: Methodsmentioning

confidence: 99%

Synthesis of the 4,7‐Dibromo Derivative of Highly Electron‐Deficient [1,2,5]Thiadiazolo[3,4‐d]pyridazine and Its Cross‐Coupling Reactions

et al. 2018

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“…We assumed that mono-adducts are insufficiently stable by the action of water or a base (K 2 CO 3 ) and the Stille coupling in non-aqueous and non-basic conditions may be successful. It was recently described that aryltributylstannanes can be easily prepared from arylboronic acids and tributyltin methoxide [35] We have found that thienylboronic ester 5 reacted with tributyltin methoxide under argon to afford thiophenetributylstannane 6 in moderate yield (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells

et al. 2019

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Four new D-A-π-A metal-free organic sensitizers for dye-sensitized solar cells (DSSCs), with [1,2,5]thiadiazolo[3 ,4-d]pyridazine as internal acceptor, thiophene unit as π-spacer and cyanoacrylate as anchoring electron acceptor, have been synthesized. The donor moiety was introduced into [1,2,5]thiadiazolo[3,4-d]pyridazine by nucleophilic aromatic substitution and Suzuki cross-coupling reactions, allowing design of D-A-π-A sensitizers with the donor attached to the internal heterocyclic acceptor not only by the carbon atom, as it is in a majority of DSSCs, but by the nitrogen atom also. Although low values of power conversion efficiency (PCE) were found, a few important consequences were identified: (i) poor PCE data can be attributed to high electron deficiency of the internal [1,2,5]thiadiazolo[3,4-d]pyridazine acceptor due to lower light harvesting by the dye; (ii) the manner in which the donor was attached to the internal acceptor (by carbon or nitrogen) did not play an essential role in the photovoltaic properties of the dyes; (iii) dyes based on the novel donor 2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazolyl and 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H- carbazole moieties showed similar photovoltaic properties to dyes based on the well-known 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indolyl building block, which opens the door for further optimization potential of new dye families.

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“…As there was a necessity to have deprotected alkynes in the reactions forming triazole products, two different methods were used for the CuAAC reaction, which avoided the isolation of potentially unstable neat terminal acetylenes. This included a previously reported in situ deprotection using sodium methoxide in the presence of catalytic amounts of copper acetate and sodium ascorbate . The other method entailed deprotection using potassium carbonate and following a work up procedure which avoided concentration of the terminal alkynes, and subjecting a toluene solution of NBD7 and NBD8 into the next step under standard CuAAC reaction conditions of cuprous iodide and Hünig's base.…”

Section: Resultsmentioning

confidence: 99%

Triazole‐Functionalized Norbornadiene‐Quadricyclane Photoswitches for Solar Energy Storage

2018

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Herein work on 2,3‐substituted norbornadiene‐quadricyclane molecular photoswitches designed for solar energy storage purposes is presented. A series of six new systems bearing 1,4‐ or 1,5‐alkyl triazoles as the acceptor unit combined with various aryl donor groups, as well as four functional intermediates, were synthesized and fully characterized. The new photoswitches were evaluated by measuring optical absorption profiles, activation energies for the thermal conversion of quadricyclanes to norbornadienes, as well as the storage energy densities. These triazoles featured a molar energy storage of 81.2–101 kJ mol–1corresponding to energy densities of 215–267 kJ kg–1. The optical absorption profiles exhibited absorption onsets up to 382 nm and a study of the thermally activated conversion from high‐energy quadricyclanes to norbornadienes revealed energy storage half lives of up to 402 days at 25 °C. The modular nature of the “click chemistry” synthesis concept used herein enables access to a large range of compounds with tailored properties such as solubility, thermal half‐life, and solar spectrum match.

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Simple preparation of aryltributylstannanes and its application to one-pot synthesis of diaryl ketones

Cited by 15 publications

References 83 publications

Synthesis of the 4,7‐Dibromo Derivative of Highly Electron‐Deficient [1,2,5]Thiadiazolo[3,4‐d]pyridazine and Its Cross‐Coupling Reactions

Synthesis of the 4,7‐Dibromo Derivative of Highly Electron‐Deficient [1,2,5]Thiadiazolo[3,4‐d]pyridazine and Its Cross‐Coupling Reactions

[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells

Triazole‐Functionalized Norbornadiene‐Quadricyclane Photoswitches for Solar Energy Storage

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