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Selective activation of 1,2-dichloroethane for access to β-chloroethylarenes enabled by nickel-catalyzed suzuki-type couplings.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Apr2019, Vol. 60 Issue 16, p1130-1134. 5p. - Publication Year :
- 2019
-
Abstract
- Graphical abstract Highlights • Nickel catalyzed Suzuki-type alkylation utilizing combined ligand systems. • Selective activation of one C–Cl bond of inert 1,2-dichloroethane (DCE). • Circumvent undesirable Ni-mediated β-chloride or β-hydride eliminations. • Facile access to homobenzylic chlorides in step-simplicities. Abstract The selective conversion of one inactive C(sp3)-Cl bond of 1,2-dichloroethane (DCE) into C(sp3)-C(sp2) linkages for access to β-chloroethylarenes is presented here. The key to achieve the required reactivity and chemoselectivity in this synthetic method was the utilization of nickel and combinatorial nitrogen ligands as catalytic system. Synthetic advantages of this coupling chemistry included the step-simplicities to β-chloroethylarenes, the mildness and effectiveness of coupling conditions, together with the convenience for allowing further functional group transformations of the retained homobenzylic C–Cl bonds. [ABSTRACT FROM AUTHOR]
- Subjects :
- *TRANSFORMATION groups
*NICKEL
*FUNCTIONAL groups
*SUZUKI reaction
*CHEMOSELECTIVITY
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 60
- Issue :
- 16
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 135596350
- Full Text :
- https://doi.org/10.1016/j.tetlet.2019.03.040