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Homogeneous Organic Reductant Based on 4,4'- t Bu 2 -2,2'-Bipyridine for Cross-Electrophile Coupling.

Authors :
Charboneau DJ
Huang H
Barth EL
Deziel AP
Germe CC
Hazari N
Jia X
Kim S
Nahiyan S
Birriel-Rodriguez L
Uehling MR
Source :
Tetrahedron letters [Tetrahedron Lett] 2024 Jul 28; Vol. 145. Date of Electronic Publication: 2024 Jun 19.
Publication Year :
2024

Abstract

The synthesis of a new homogeneous reductant based on 4,4'- <superscript>t</superscript> Bu <subscript>2</subscript> -2,2'-bipyridine, <superscript>t</superscript> Bu-OED <subscript>4</subscript> , is reported. <superscript>t</superscript> Bu-OED <subscript>4</subscript> was prepared on a multigram scale in two steps from inexpensive and commercially available starting materials, with no chromatography required for purification. <superscript>t</superscript> Bu-OED <subscript>4</subscript> has a reduction potential of -1.33 V (vs Ferrocenium/Ferrocene) and is soluble in a range of common organic solvents. We demonstrate that <superscript>t</superscript> Bu-OED <subscript>4</subscript> can facilitate Ni/Co dual-catalyzed C(sp <superscript>2</superscript> )-C(sp <superscript>3</superscript> ) cross-electrophile coupling reactions and is highly functional group tolerant. <superscript>t</superscript> Bu-OED <subscript>4</subscript> is expected to be a valuable addition to the set of homogeneous reductants available for organic transformations.<br />Competing Interests: Competing Financial Interests The authors declare no competing financial interests. Declaration of interests The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Details

Language :
English
ISSN :
0040-4039
Volume :
145
Database :
MEDLINE
Journal :
Tetrahedron letters
Publication Type :
Academic Journal
Accession number :
39036418
Full Text :
https://doi.org/10.1016/j.tetlet.2024.155159