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
. 2016 Jul 18;22(30):10410-4.
doi: 10.1002/chem.201602088. Epub 2016 Jun 20.

Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles

Xiaoxun Li  1 , Haibo Xie  1 , Xiaoning Fu  2 , Ji-Tian Liu  1 , Hao-Yuan Wang  1 , Bao-Min Xi  3 , Peng Liu  4 , Xiufang Xu  5 , Weiping Tang  6   7
Affiliations

Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles

Xiaoxun Li et al. Chemistry. .

Abstract

A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4-C7 positions of indoles and related heterocycles.

Keywords: annulation; carbonylation; catalysis; indoles; rhodium.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Strategies for the Synthesis of Indoles and Related Heterocycles
Scheme 2
Scheme 2
Further Functionalization of Indoles Derivatives
Scheme 3
Scheme 3
Effect of Ester for the Benzannulation Reaction
Scheme 4
Scheme 4
Proposed Mechanism Based on Previous [5+2] Cycloaddition of 3-Acyloxy-1,4-enynes and Alkynes
Scheme 5
Scheme 5
Gibbs Free Energy Profiles for 1,2-Acyloxy Migration. Energies Are in kcal/mol and Calculated Using B3LYP/SDD-6-31G(d)/SMD(CH2Cl2)
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. For selected reviews on indole synthesis, see: Barluenga J, Rodriguez F, Fananas FJ. Chem Asian J. 2009;4:1036.Taber DF, Tirunahari PK. Tetrahedron. 2011;67:7195.Vicente R. Org Biomol Chem. 2011;9:6469.Platon M, Amardeil R, Djakovitch L, Hierso JC. Chem Soc Rev. 2012;41:3929.

    1. For a leading reference on de novo synthesis of polysubstituted benzenes, see: Izawa Y, Pun D, Stahl SS. Science. 2011;333:209.For a recent example on making indoles by benzannulation, see: Lam TY, Wang Y-P, Danheiser RL. J Org Chem. 2013;78:9396.

    1. Dötz KH. Angew Chem Int Ed. 1975;14:644.Dötz KH. Angew Chem Int Ed. 1984;23:587.Wulff WD, Tang PC, Chan KS, McCallum JS, Yang DC, Gilbertson SR. Tetrahedron. 1985;41:5813.

    1. For recent reviews on reactions involving Fischer carbenes, see: Gomez-Gallego M, Mancheno MJ, Sierra MA. Acc Chem Res. 2005;38:44.Dötz KH, Stendel J., Jr Chem Rev. 2009;109:3227.

    1. Wulf WD. In: Advances in Metal-Organic Chemistry. Liebeskind LS, editor. Vol. 1. JAI Press; Greenwich, CT: 1989. p. 336.
    2. Lian YQ, Wulff WD. J Am Chem Soc. 2005;127:17162. - PMC - PubMed
    3. Merlic CA, Xu DQ. J Am Chem Soc. 1991;113:7418.
    4. Merlic CA, Burns EE, Xu DQ, Chen SY. J Am Chem Soc. 1992;114:8722.

LinkOut - more resources