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Catalytic Reductions without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2019-12-30 , DOI: 10.1002/adsc.201901549
Kirill A. Korvinson 1, 2 , Hari K. Akula 1 , Casina T. Malinchak 1, 2 , Dellamol Sebastian 1, 2 , Wei Wei 1, 2 , Tashrique A. Khandaker 1 , Magdalena R. Andrzejewska 1 , Barbara Zajc 1, 2 , Mahesh K. Lakshman 1, 2
Affiliation  

The inside cover picture, designed by Lakshman and co‐workers, illustrates a diverse set of hydrogenations that can be conducted without use of external hydrogen gas (compressed gas). 4‐Methylmorpholine (NMM), tetrahydroxydiboron [B2(OH)4], and 5% Pd on charcoal work in concert to cause reductions of aryl halides and triflates, alkenes, alkynes, aldehydes, and azides, as well as cleavage of benzylic ethers and N‐Cbz groups. Based on the mechanistic knowledge gained in the study, aromatic deuteriations have also been accomplished using N,N‐bis(methyl‐d3)pyridin‐4‐amine (DMAP‐d6) and B2(OD)4. H2 gas appears to be formed in these reactions and this has been observed by 1H NMR and GC analysis. Details of this work can in found in the full paper on pages 166–176 (K. A. Korvinson, H. K. Akula, C. T. Malinchak, D. Sebastian, W. Wei, T. A. Khandaker, M. R. Andrzejewska, B. Zajc, M. K. Lakshman, Adv. Synth. Catal. 2020, 362, 166–176; DOI: 10.1002/adsc.201901099).
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中文翻译:

在没有外部氢气的情况下进行催化还原:使用四羟基二硼和叔胺进行大范围加氢

由Lakshman及其同事设计的内页封面图片展示了可以在使用外部氢气(压缩气体)的情况下进行的多种氢化反应。4-甲基吗啉(NMM),四羟基二硼[B 2(OH)4 ]和5%的钯在木炭上协同作用,导致芳基卤化物和三氟甲磺酸酯,烯烃,炔烃,醛和叠氮化物的还原,以及苄基的裂解醚和N- Cbz基团。根据研究中获得的机理知识,还可以使用NN-双(甲基-d 3)吡啶-4-胺(DMAP- d 6)实现芳族氘化)和B 2(OD)4。在这些反应中似乎形成了H 2气体,这已通过1 H NMR和GC分析观察到。这项工作的详细信息可以在第166-176页的全文中找到(KA Korvinson,HK Akula,CT Malinchak,D.Sebastian,W.Wei,TA Khandaker,MR Andrzejewska,B.Zajc,MK Lakshman,Adv.Synth 。CATAL2020362,166-176; DOI:10.1002 / adsc.201901099)。
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更新日期:2019-12-30
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