Charboneau David J, Huang Haotian, Barth Emily L, Deziel Anthony P, Germe Cameron C, Hazari Nilay, Jia Xiaofan, Kim Seoyeon, Nahiyan Sheikh, Birriel-Rodriguez Leonardo, Uehling Mycah R
Department of Chemistry, Yale University, P. O. Box 208107, New Haven, Connecticut, 06520, USA.
Merck & Co., Inc., Discovery Chemistry, HTE and Lead Discovery Capabilities, Rahway, New Jersey, 07065, USA.
Tetrahedron Lett. 2024 Jul 28;145. doi: 10.1016/j.tetlet.2024.155159. Epub 2024 Jun 19.
The synthesis of a new homogeneous reductant based on 4,4'-Bu-2,2'-bipyridine, Bu-OED, is reported. Bu-OED was prepared on a multigram scale in two steps from inexpensive and commercially available starting materials, with no chromatography required for purification. Bu-OED has a reduction potential of -1.33 V (vs Ferrocenium/Ferrocene) and is soluble in a range of common organic solvents. We demonstrate that Bu-OED can facilitate Ni/Co dual-catalyzed C(sp)-C(sp) cross-electrophile coupling reactions and is highly functional group tolerant. Bu-OED is expected to be a valuable addition to the set of homogeneous reductants available for organic transformations.
报道了一种基于4,4'-二叔丁基-2,2'-联吡啶（Bu-OED）的新型均相还原剂的合成。Bu-OED由廉价且市售的起始原料分两步以多克规模制备，纯化无需色谱法。Bu-OED的还原电位为-1.33 V（相对于二茂铁鎓/二茂铁），可溶于一系列常见有机溶剂。我们证明Bu-OED能够促进镍/钴双催化的C(sp)-C(sp)交叉亲电偶联反应，并且对官能团具有高度耐受性。预计Bu-OED将成为有机转化可用的均相还原剂中的一种有价值的补充。
