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Mairhofer, Christopher, David Naderer, and Mario Waser. Beilstein Journal of Organic Chemistry 20.1 (2024): 1510-1517.
In this study, tetrabutylammonium iodide (TBAI) was employed as a phase-transfer catalyst to facilitate the oxidative α-azidation of cyclic β-ketocarbonyl compounds using sodium azide (NaN3) in the presence of dibenzoyl peroxide (BPO). The reaction proceeds under mild conditions in dichloroethane (DCE) at room temperature, providing an operationally simple and efficient route to α-azidated carbonyl derivatives with high yields and purity.
Mechanistic investigations indicate that TBAI mediates the in situ formation of an ammonium hypoiodite species, which initially promotes α-iodination of the carbonyl pronucleophile. Subsequent nucleophilic substitution by azide occurs via a phase-transfer process, effectively leveraging TBAI to enhance reaction kinetics and selectivity. Control experiments and comparative studies confirmed that TBAI's dual role-both as an iodide source and as a phase-transfer facilitator-is critical for the success of the transformation.
The use of TBAI allows for the direct functionalization of carbonyl compounds without requiring harsh conditions or pre-activation steps, offering a versatile platform for the introduction of azido groups. Moreover, the methodology demonstrates adaptability, as analogous α-nitration reactions using sodium nitrite (NaNO2) are achievable under similar conditions, highlighting TBAI's broader applicability in oxidative functionalization chemistry.
Overall, tetrabutylammonium iodide proves to be a highly effective reagent for enabling selective α-functionalization of carbonyl compounds via phase-transfer catalysis, providing a practical and scalable approach for synthetic applications in medicinal chemistry and materials science.
Zheng, Shenshen, et al. Solar Energy 230 (2021): 666-674.
In this study, tetrabutylammonium iodide (TBAI) was employed as a surface passivation agent to enhance the performance and stability of all-inorganic carbon-based perovskite solar cells (C-PSCs) utilizing CsPbI2Br as the photosensitizer. CsPbI2Br films prepared by solution processing often suffer from defects and voids, which impede charge extraction and reduce device efficiency. TBAI treatment interacts with the Pb-I framework at the film surface, passivating defect states and prolonging carrier lifetime, thereby improving overall device performance.
The CsPbI2Br films were fabricated via a sequential graded thermal annealing combined with ethyl acetate antisolvent treatment to achieve uniform, high-crystallinity films with minimal voids. Post-deposition, TBAI in isopropyl alcohol was spin-coated onto the cold perovskite films and annealed, resulting in effective surface defect passivation. The optimized C-PSCs exhibited a champion power conversion efficiency (PCE) of 12.29% under ambient conditions, highlighting TBAI's ability to improve both charge transport and collection.
In addition to performance enhancement, TBAI significantly improved device stability. Unencapsulated TBAI-treated PSCs retained 90% of their initial PCE after 300 hours of storage in ambient air with 20-30% relative humidity. The study demonstrates that tetrabutylammonium iodide not only serves as an efficient defect passivation agent but also as a stability enhancer, offering a simple and scalable strategy for producing low-cost, high-performance, and stable all-inorganic PSCs suitable for commercialization.
This case exemplifies TBAI's critical role in perovskite optoelectronics, where molecular-level surface engineering translates directly into macroscopic device efficiency and longevity.
Yu, Dong, et al. Tetrahedron Letters 59.40 (2018): 3620-3623.
In this study, tetrabutylammonium iodide (TBAI) was employed as a highly effective and environmentally benign catalyst for the hydroxylation of naphthoquinone derivatives, using tert-butyl hydroperoxide (TBHP) as the oxidant. This methodology enables the efficient synthesis of various hydroxylated naphthoquinone compounds, which serve as key intermediates in pharmaceutical applications, including the drugs parvaquone and lapachol.
The reaction was optimized using 2-methyl-1,4-naphthoquinone (vitamin K3) as the model substrate. Under optimal conditions-TBAI (40 mol%), TBHP (3 equiv), and THF as solvent at 120 °C for 24 hours in a sealed tube-the desired hydroxylated product was obtained in 88% isolated yield. Control experiments demonstrated the critical role of TBAI, as substitution with other catalysts (e.g., TBAB, KI, I2) led to significantly lower yields or no reaction. Alternative oxidants and solvents were also less effective, underscoring the unique synergistic effect of TBAI and TBHP in THF for promoting this transformation.
The mechanism likely involves in situ generation of an iodide-activated species, facilitating selective hydroxylation at the α-position of naphthoquinone derivatives. This operationally simple and scalable protocol provides a sustainable approach for preparing pharmaceutically relevant hydroxylated compounds, demonstrating TBAI's versatility in phase-transfer and oxidative catalysis.
This case study highlights tetrabutylammonium iodide as a robust catalytic tool for green and efficient organic transformations, with direct implications for drug synthesis and fine chemical production.
