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Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A Multifunctional Catalyst
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-03-23 , DOI: 10.1021/acs.joc.0c00234
Nabin Sarkar 1 , Subhadeep Bera 1 , Sharanappa Nembenna 1
Affiliation  

The reaction of LH [L = {(ArNH)(ArN)–C=N–C=(NAr)(NHAr)}; Ar =2,6-Et2-C6H3] with a commercially available alane amine adduct (H3Al·NMe2Et) in toluene resulted in the formation of a conjugated bis-guanidinate (CBG)-supported aluminum dihydride complex, i.e., LAlH2 (1), in good yield. The new complex has been thoroughly characterized by multinuclear magnetic resonance, IR, mass, and elemental analyses, including single-crystal structural studies. Further, we have demonstrated the aluminum-catalyzed hydroboration of a variety of nitriles and alkynes. Moreover, aluminum-catalyzed hydroboration is expanded to more challenging substrates such as alkene, pyridine, imine, carbodiimide, and isocyanides. More importantly, we have shown that the aluminum dihydride catalyzed both intra- and intermolecular chemoselective hydroboration of nitriles and alkynes over other reducible functionalities for the first time.

中文翻译:

铝催化腈和炔烃的选择性加氢硼化:多功能催化剂

LH的反应[L = {((ArNH)(ArN)–C = NC–(NAr)(NHAr)}};Ar = 2,6-Et 2 -C 6 H 3 ]与可商购的烷胺在甲苯中的加合物(H 3 Al·NMe 2 Et)导致形成共轭双胍盐(CBG)负载的二氢氧化铝配合物即LAlH 21),产量高。新的复合物已通过多核磁共振,IR,质量和元素分析(包括单晶结构研究)进行了全面表征。此外,我们已经证明了铝催化的各种腈和炔烃的硼氢化反应。而且,铝催化的硼氢化反应扩展到更具挑战性的底物,例如烯烃,吡啶,亚胺,碳二亚胺和异氰化物。更重要的是,我们首次证明,二氢氧化铝催化腈和炔烃的分子内和分子间化学选择性氢硼化反应优于其他可还原官能团。
更新日期:2020-03-24
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