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
. 2013 Apr;69(13):2701-2713.
doi: 10.1016/j.tet.2013.02.003.

Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions

Nataliya A Markina  1 , Yu Chen, Richard C Larock
Affiliations

Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions

Nataliya A Markina et al. Tetrahedron. 2013 Apr.

Abstract

An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues.

Keywords: Sonogashira coupling; benzofuran; microwave; three-component reaction.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
A one-pot approach to benzofurans using MeMgCl
Scheme 2
Scheme 2
An alternative route employing 4-ethynylbenzonitrile
Scheme 3
Scheme 3
Synthesis of benzofurans from iodophenols, alkynes and alkenes
Scheme 4
Scheme 4
Pd-catalyzed diversification
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For recent selected examples, see: Boto A, Alvarez L. Heterocycles in Nat. Prod. Synthesis. 2011:99–152.. Ashwood VA, Field MJ, Horwell DC, Julien-Larose C, Lewthwaite RA, McCleary S, Pritchard MC, Raphy J, Singh L. J. Med. Chem. 2001;44:2276–2285..

    1. For some recent comprehensive reviews on the synthesis of benzofurans, see:Cacchi S, Fabrizi G, Goggiamani A. Org. Biomol. Chem. 2011;9:641–652.. Yeung K-S, Peng S-X, Wu J, Hou X-L. Prog. Heterocycl. Chem. 2011;23:195–229.. Wu J. Five-membered Heterocycles: Benzofuran and Related Systems. Modern Heterocyclic Chemistry; 2011. pp. 593–633.. Mentwally MA, Abdel-Wahab BF, Al-Hiti GA. Curr. Org. Chem. 2010;14:48–64.. Miyata O, Takeda N, Naito T. Heterocycles. 2009;78:843–871.. De Luca L, Nieddu G, Porcheddu A, Giacomelli G. Curr. Med. Chem. 2009;16:1–20. and references therein..

    1. Majumdar KC, Chattopadhyay B, Maji PK, Chattopadhyay SK, Samanta S. Heterocycles. 2010;81:517–584.
    2. Cacchi S, Fabrizi G, Goggiamani A. Curr. Org. Chem. 2006;10:1423–1455.
    3. Dudnik AS, Gevorgyan V. Catalyzed Carbon-Heteroatom Bond Formation. 2011:317–410.

    4. d)For examples of Pd-catalyzed C-H activation leading to benzofuran formation, see:Ferreira EM, Zhang H, Stoltz BM. Tetrahedron. 2008;64:5987–6001..

    1. Arcadi A, Cacchi S, Del Rosario M, Fabrizi G, Marinelli F. J. Org. Chem. 1996;61:9280–9288.
    1. Chaplin JH, Flynn BL. Chem. Commun. 2001:1594–1595. - PubMed

LinkOut - more resources