Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone,Applied Organometallic Chemistry

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Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone
Applied Organometallic Chemistry ( IF 3.7 ) Pub Date : 2020-11-17 , DOI: 10.1002/aoc.6105
Kihyuk Sung ₁ , Mi‐hyun Lee ₁ , Yeon‐Joo Cheong ₁ , Hye‐Young Jang ₁

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Sustainable iridium‐catalyzed transfer hydrogenation using glycerol as the hydride source was employed to convert levulinic acid to γ‐valerolactone (GVL) with exceptionally high turnover numbers (TONs) (500,000) and turnover frequencies (TOFs) (170,000 h⁻¹). The highly efficient triscarbene‐modified iridium catalysts demonstrated good catalytic activities with low catalyst loadings (0.7 ppm) and good recyclability with an accumulated TON of over two million in the fourth reaction. In addition to glycerol, propylene glycol (PG), ethylene glycol (EG), isopropanol (IPA), and ethanol (EtOH) successfully transferred hydrides to levulinic acid, producing GVL with TONs of 339,000 (PG), 242,000 (EG), 334,000 (IPA), and 208,000 (EtOH), respectively. Deuterium‐labeling experiments were conducted to gain insight into the reaction mechanism.

中文翻译：

Ir（三碳卡宾）催化的乙酰丙酸可持续转移加氢成γ-戊内酯

以甘油为氢化物源的可持续铱催化转移加氢被用于将乙酰丙酸转化为具有极高周转率（TONs）（500,000）和周转率（TOFs）（170,000 h ^-1的γ-戊内酯（GVL））。高效的三卡宾改性铱催化剂表现出良好的催化活性和较低的催化剂负载量（0.7 ppm），并且具有良好的可回收性，在第四次反应中的累积TON超过200万。除甘油外，丙二醇（PG），乙二醇（EG），异丙醇（IPA）和乙醇（EtOH）成功地将氢化物转移到乙酰丙酸中，生产出TON值为339,000（PG），242,000（EG），334,000的GVL （IPA）和208,000（EtOH）。进行氘标记实验以深入了解反应机理。

更新日期：2020-11-17

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