Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Jan 11;60(2):670-674.
doi: 10.1002/anie.202011708. Epub 2020 Nov 10.

Amino-Supported Palladium Catalyst for Chemo- and Stereoselective Domino Reactions

Man-Bo Li  1 , Jie Yang  2 , Ying Yang  1 , Guo-Yong Xu  1 , Gen Luo  1 , Jianping Yang  3 , Jan-E Bäckvall  2   4
Affiliations

Amino-Supported Palladium Catalyst for Chemo- and Stereoselective Domino Reactions

Man-Bo Li et al. Angew Chem Int Ed Engl. .

Abstract

A solid amino-supported palladium catalyst is used in an oxidative domino reaction for the diastereoselective construction of alkyne-substituted cyclopentenol compounds. This heterogeneous catalyst exhibits high efficiency and excellent chemoselectivity, as well as good recyclability. The chemoselectivity of the domino reactions was readily controlled by switching the solvent and catalyst. Asymmetric syntheses and an oxidative carbocyclization-borylation reaction have also been developed based on the heterogeneous palladium catalyst.

Keywords: amines; cyclizations; heterogeneous catalysis; palladium; supported catalysts.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Proposed domino process, selectivity challenge, and representative bioactive compounds.
Figure 1
Figure 1
XPS Pd3d spectra of the reaction mixture by using Pd(OAc)2 (a: before reaction; b: after reaction) or Pd‐AmP‐MCF (c: before reaction; d: after reaction) as the catalyst. Inset: Photos of the reaction mixture. e) An illustration of the heterogeneous catalyst and its three‐in‐one role.
Scheme 2
Scheme 2
Substrate scope for the synthesis of 2. [a] Without Et3N.
Figure 2
Figure 2
Rrecycling experiments and kinetic studies.
Scheme 3
Scheme 3
Chemodivergent syntheses of 3, 4 and 5. [a] 5 mol % of Pd(OAc)2. [b] 1 mol % of Pd(OAc)2, starting materials were partially recovered. [c] 1 mol % of Pd‐AmP‐MCF. [d]>90 % conversion, 2 was obtained as the byproducts.
Scheme 4
Scheme 4
Applications of the solid palladium catalyzed domino process.
Scheme 5
Scheme 5
Proposed mechanism.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Tietze L. F., Brasche G., Gericke K., Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2008.
    1. Tietze L. F., Domino Reactions: Concepts for Efficient Organic Synthesis, Wiley-VCH, Weinheim, 2014.
    1. Nicolaou K. C., Edmonds D. J., Bulger P. G., Angew. Chem. Int. Ed. 2006, 45, 7134–7186; - PubMed
    2. Angew. Chem. 2006, 118, 7292–7344.
    1. Grondal C., Jeanty M., Enders D., Nat. Chem. 2010, 2, 167–178. - PubMed
    1. Volla C. M. R., Atodiresei I., Rueping M., Chem. Rev. 2014, 114, 2390–2431. - PubMed

LinkOut - more resources