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Synthesis, characterisation, and catalytic application of a soluble molecular carrier of sodium hydride activated by a substituted 4-(dimethylamino)pyridine
Communications Chemistry ( IF 5.9 ) Pub Date : 2024-04-27 , DOI: 10.1038/s42004-024-01184-5
Peter A. Macdonald , Alan R. Kennedy , Catherine E. Weetman , Stuart D. Robertson , Robert E. Mulvey

Recently main group compounds have stepped into the territory of precious transition metal compounds with respect to utility in the homogeneous catalysis of fundamentally important organic transformations. Inspired by the need to promote more sustainability in chemistry because of their greater abundance in nature, this change of direction is surprising since main group metals generally do not possess the same breadth of reactivity as precious transition metals. Here, we introduce the dihydropyridylsodium compound, Na-1,2-tBu-DH(DMAP), and its monomeric variant [Na-1,2-tBu-DH(DMAP)]·Me6TREN, and demonstrate their effectiveness in transfer hydrogenation catalysis of the representative alkene 1,1-diphenylethylene to the alkane 1,1-diphenylethane using 1,4-cyclohexadiene as hydrogen source [DMAP = 4-dimethylaminopyridine; Me6TREN = tris(N,N-dimethyl-2-aminoethyl)amine]. Sodium is appealing because of its high abundance in the earth’s crust and oceans, but organosodium compounds have been rarely used in homogeneous catalysis. The success of the dihydropyridylsodium compounds can be attributed to their high solubility and reactivity in organic solvents.



中文翻译:

取代4-(二甲氨基)吡啶活化氢化钠可溶性分子载体的合成、表征及催化应用

最近,主族化合物已进入贵重过渡金属化合物的领域,在基本重要的有机转化的均相催化中具有实用性。由于自然界中化学物质的丰富程度较高,因此需要促进化学的可持续性,这种方向的改变是令人惊讶的,因为主族金属通常不具有与贵金属过渡金属相同的反应性。在这里,我们介绍了二氢吡啶基钠化合物Na-1,2- t Bu-DH(DMAP)及其单体变体[Na-1,2- t Bu-DH(DMAP)]·Me 6 TREN,并证明了它们的有效性以1,4-环己二烯为氢源,将代表性烯烃1,1-二苯基乙烯转移加氢催化为烷烃1,1-二苯基乙烷[DMAP = 4-二甲基氨基吡啶; Me 6 TREN = 三( N , N-二甲基-2-氨基乙基)胺]。钠因其在地壳和海洋中的丰富度而备受关注,但有机钠化合物很少用于均相催化。二氢吡啶钠化合物的成功可归因于它们在有机溶剂中的高溶解度和反应活性。

更新日期:2024-04-28
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