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Heterogeneous asymmetric β-C-H functionalization of aldehydes under O2 catalyzed by hydroxide-layered Fe(III) sites synergistic with confined interlayer amine.
- Source :
-
Journal of Catalysis . Oct2022, Vol. 414, p267-276. 10p. - Publication Year :
- 2022
-
Abstract
- A strategy for one-pot asymmetric β-C-H functionalization of aldehydes under O 2 has been proposed, catalysed by the hydroxide-layered Fe(III) sites synergistic with confined interlayer amines through a cascade oxidation-addition process. [Display omitted] • First proposal of a heterogeneous strategy to boost the one-pot asymmetric β-C-H functionalization of aldehyde under O 2 using hydroxide-layered Fe(III) sites synergistic with confined interlayer amine. • Achievements of an excellent regioselectivity (>99%), a good stereoselectivity (90%), and a moderate yield (65%) for the major β-functionalized diastereomer. • Good reusability of the L-proline intercalated Fe(III)-containing LDHs in the heterogeneous catalysis. Asymmetric functionalization of inert β-C-H is one of the most powerful strategies in organic synthesis, but of great challenge in the efficient β-C-H activation and the enantioselective C-heteroatom formation. Here, this work proposes an elegant strategy for one-pot asymmetric β-C-H functionalization of aldehyde under O 2 catalyzed by hydroxide-layered Fe(III) sites synergistic with confined interlayer amine through a cascade oxidation-addition process on L-proline intercalated Fe-containing layered double hydroxides (LDHs), in which the direct β-H elimination of aldehyde on hydroxide-layered Fe(III) sites with the two-electron abstraction promoted by the Fe(III):N coordination as the key step to efficiently oxidize the enamine. The major β-functionalized diastereomer in the asymmetric nitromethylation of 3-phenylpropanal has been afforded in a regioselectivity of up to >99%, a stereoselectivity of 90%, and a yield of 65% on L-proline intercalated Mg 3.00 Al 0.47 Fe 0.45 -LDHs. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00219517
- Volume :
- 414
- Database :
- Academic Search Index
- Journal :
- Journal of Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 159693260
- Full Text :
- https://doi.org/10.1016/j.jcat.2022.09.009