Research Progress in Reduction of Alkenes and Alkynes by Sodium Borohydride
LU Baohua1, XU Ning1, CHEN Xiaotong1, XIE Xiaohong1, LI Jiuming1,2,3
1 College of Chemistry and Materials, Inner Mongolia University for Nationalities, Tongliao 028000, China 2 Inner Mongolia Industrial Engineering Research Center of Universities for Castor, Tongliao 028000, China 3 Inner Mongolia Key Laboratory for the Natural Products Chemistry and Functional Molecular Synthesis, Tongliao 028000, China
Abstract: Catalytic hydrogenation of unsaturated hydrocarbons has always been an important approach to prepare compounds which can not be obtained from nature, which is extreme important in industrial production and researches. Traditional hydrogenation of unsaturated hydrocarbons not only requires catalysts, but also higher reaction temperature and hydrogen pressure are needed, the reaction conditions are relatively harsh, which is not only extreme strict for reaction equipment, but also has obvious issues of potential safety in the reaction. Therefore, it is necessary to explore a catalytic system with mild reaction conditions and excellent catalytic effect. NaBH4 was discovered by Brown at the University of Chicago in 1942. Organic borohydride is generally applied to reduce the carbonyl groups of aldehydes and ketones as cheap, safe, stable, easily handling and highly reductive. In 1962, Brown first reported the reduction of simple alkynes by NaBH4 in the presence of catalyst. This is the first example of NaBH4 as a hydrogen donor for the reduction of unsaturated hydrocarbons, an alternative method for the reduction of unsaturated hydrocarbons was found. NaBH4 can reduce unsaturated hydrocarbons based on catalysts. The catalysts can be divided into precious metal and non-precious metal catalysts. The precious metal catalysts are mainly Pd, In, Ru and other metals, while the non-precious metals mainly include Cu, Co, Ni and other metals. Precious metal and non-precious metal catalysts are metal salts or metal nanoparticles supported on carrier, which have high catalytic activity and chemical stability. At first, precious metal catalysts were mainly studied, however the price of precious metal catalysts was relatively high, some precious metal catalysts were deactivated after application. Non-precious metal catalysts are gradually becoming the focus as researches continue, which are not only cheap, but also have similar catalytic effect with precious metal catalysts. Now, the conversion rate of unsaturated hydrocarbon can be boosted up to 99% in precious metal catalyst/NaBH4 catalytic system, 98% conversion rate can be achieved in non-precious metal catalyst/NaBH4 catalytic system. It can be noted that the conversion rate and catalytic activity of the two catalysts are basically same. Therefore, non-precious metal catalysts can be applied instead of precious metal catalysts without special requirements. Here the essay reviews recent research results and advancements of alkenes and alkynes by NaBH4 under various non-precious metal/precious metal catalysts, including the alkynes and alkynes containing sensitive protective groups. The reduction of alkynes and alkynes by sodium borohydride are briefly introduced, summarized and prospected.
作者简介: 芦宝华,2017年6月毕业于河套学院,获得理学学士学位。现为内蒙古民族大学化学与材料学院硕士研究生,在李久明教授的指导下进行研究。目前主要研究领域为金属纳米粒子催化NaBH4还原烯烃。 李久明,内蒙古民族大学化学化工学院教授,硕士研究生导师。1994年7月本科毕业于内蒙古民族师范学院,2008年7月毕业于中国科学院新疆理化技术研究所有机化学专业并获得博士学位,博士毕业后执教于内蒙古民族大学化学与材料学院。主要从事天然产物的提取分离及结构鉴定、精细化学品的合成与应用、化学农药与生物农药的研发应用等研究。近年来发表论文20余篇,包括Chemistry of Natural Compounds、Acta Cryst、Industrial Crops and Products等。
引用本文:
芦宝华, 徐宁, 陈晓彤, 谢晓红, 李久明. 硼氢化钠还原烯烃和炔烃的研究进展[J]. 材料导报, 2021, 35(5): 5214-5221.
LU Baohua, XU Ning, CHEN Xiaotong, XIE Xiaohong, LI Jiuming. Research Progress in Reduction of Alkenes and Alkynes by Sodium Borohydride. Materials Reports, 2021, 35(5): 5214-5221.
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2021, Vol. 35 
