Homogeneous Organic Reductant Based on 4,4'-tBu2-2,2'-Bipyridine for Cross-Electrophile Coupling
David J Charboneau1, Haotian Huang1, Emily L Barth1
1Department of Chemistry, Yale University, P. O. Box 208107, New Haven, Connecticut, 06520, USA.
Abstract:
The synthesis of a new homogeneous reductant based on 4,4'-tBu2-2,2'-bipyridine, tBu-OED4, is reported. tBu-OED4 was prepared on a multigram scale in two steps from inexpensive and commercially available starting materials, with no chromatography required for purification. tBu-OED4 has a reduction potential of -1.33 V (vs Ferrocenium/Ferrocene) and is soluble in a range of common organic solvents. We demonstrate that tBu-OED4 can facilitate Ni/Co dual-catalyzed C(sp2)-C(sp3) cross-electrophile coupling reactions and is highly functional group tolerant. tBu-OED4 is expected to be a valuable addition to the set of homogeneous reductants available for organic transformations.
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