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Iron-catalysed hydroalumination of internal alkynes
Chemical Science ( IF 8.4 ) Pub Date : 2022-06-13 , DOI: 10.1039/d2sc02160a
Wen-Tao Li 1 , Meng-Yang Hu 1 , Jun-Wen Xiong 1 , Xin-Yu Zhang 1 , Shou-Fei Zhu 1, 2
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Although research on iron-catalysed reactions has recently achieved significant progress, the activity and selectivity of iron catalysts are generally inferior to those of noble-metal catalysts. The development of new iron-catalysed reactions, especially those in which iron catalysts exhibit superior activity or selectivity to other catalysts, is the key to promote iron catalysis. Herein, we report the first protocol for iron-catalysed hydroalumination of internal alkynes. Specifically, in the presence of iron catalysts bearing 2,9-diaryl-1,10-phenanthroline ligands, internal alkynes were stereo- and regioselectively hydroaluminated with the commercially available reagent diisobutylaluminum hydride. Compared with other metal-catalysed alkyne hydroalumination reactions reported in the literature, the iron-catalysed protocol has the following advantages: unusual amino-group-directed regioselectivity, a wide substrate scope, good functional group tolerance, high selectivity, and mild reaction conditions. The alkenylaluminum products prepared in this way could undergo a diverse array of transformations, and were used for the synthesis of bioactive compounds. The current study expands the scope of iron catalysis, provides a new efficient access to alkenylaluminum, discloses the origin of the superiority of iron catalysts, and thus may inspire further studies in related fields.

中文翻译:

内炔烃的铁催化氢化铝化

尽管最近对铁催化反应的研究取得了重大进展,但铁催化剂的活性和选择性普遍不如贵金属催化剂。开发新的铁催化反应,特别是那些铁催化剂表现出优于其他催化剂的活性或选择性的反应,是促进铁催化的关键。在此,我们报告了第一个铁催化内部炔烃氢化铝化的方案。具体而言,在带有 2,9-二芳基-1,10-菲咯啉配体的铁催化剂存在下,内部炔烃用市售试剂氢化二异丁基铝进行立体选择性和区域选择性氢化铝化。与文献报道的其他金属催化的炔烃氢化铝化反应相比,铁催化方案具有以下优点:不寻常的氨基定向区域选择性、广泛的底物范围、良好的官能团耐受性、高选择性和温和的反应条件。以这种方式制备的烯基铝产品可以进行多种转化,并用于生物活性化合物的合成。本研究拓宽了铁催化的范围,为烯基铝提供了一种新的高效途径,揭示了铁催化剂优越性的由来,可能会启发相关领域的进一步研究。并用于合成生物活性化合物。本研究拓宽了铁催化的范围,为烯基铝提供了一种新的高效途径,揭示了铁催化剂优越性的由来,可能会启发相关领域的进一步研究。并用于合成生物活性化合物。本研究拓宽了铁催化的范围,为烯基铝提供了一种新的高效途径,揭示了铁催化剂优越性的由来,可能会启发相关领域的进一步研究。
更新日期:2022-06-13
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