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
. 2014 Mar 21;79(6):2781-91.
doi: 10.1021/jo500252e. Epub 2014 Mar 12.

Development of a Suzuki cross-coupling reaction between 2-azidoarylboronic pinacolate esters and vinyl triflates to enable the synthesis of [2,3]-fused indole heterocycles

Navendu Jana  1 , Quyen Nguyen, Tom G Driver
Affiliations

Development of a Suzuki cross-coupling reaction between 2-azidoarylboronic pinacolate esters and vinyl triflates to enable the synthesis of [2,3]-fused indole heterocycles

Navendu Jana et al. J Org Chem. .

Abstract

The scope and limitations of a Suzuki reaction between 2-azidoarylboronic acid pinacolate esters and vinyl triflates are reported. This cross-coupling reaction enables the regioselective synthesis of indoles after a subsequent Rh(II)2-catalyzed sp(2)-C-H bond amination reaction.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Cross-Coupling Strategies That Synthesize 2-Alkenyl Aryl Azides
Scheme 2
Scheme 2. Investigation of the Scope and Limitations of the Cross-Coupling of 2-Azidoarylboron Pincolate Esters with Vinyl Triflates
Reaction performed on a 4 mmol scale.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. For reviews, see:

    2. Gribble G. W.; Saulnier M. G.; Pelkey E. T.; Kishbaugh T. L. S.; Liu Y.; Jiang J.; Trujillo H. A.; Keavy D. J.; Davis D. A.; Conway S. C.; Switzer F. L.; Roy S.; Silva R. A.; Obaza-Nutaitis J. A.; Sibi M. P.; Moskalev N. V.; Barden T. C.; Chang L.; Habeski (née Simon) W. M.; Pelcman B.; Sponholtz W. R. III; Chau R. W.; Allison B. D.; Garaas S. D.; Sinha M. S.; McGowan M. A.; Reese M. R.; Harpp K. S. Curr. Org. Chem. 2005, 9, 1493.
    3. Agarwal S.; Cämmerer S.; Filali S.; Fröhner W.; Knöll J.; Krahl M. P.; Reddy K. R.; Knölker H.-J. Curr. Org. Chem. 2005, 9, 1601.
    4. Crich D.; Banerjee A. Acc. Chem. Res. 2007, 40, 151. - PubMed
    5. Edwankar C. R.; Edwankar R. V.; Namjoshi O. A.; Rallapappi S. K.; Yang J.; Cook J. M. Curr. Opin. Drug Discuss. Dev. 2009, 12, 752. - PubMed
    6. Bandini M.; Eichholzer A. Angew. Chem., Int. Ed. 2009, 48, 9608. - PubMed
    7. Ruiz-Sanchis P.; Savina S. A.; Albericio F.; Álvarez M. Chem. Eur. J. 2011, 17, 1388. - PubMed
    8. Taber D. F.; Tirunahari P. K. Tetrahedron 2011, 67, 7195. - PMC - PubMed
    9. Schmidt A. W.; Reddy K. R.; Knölker H.-J. Chem. Rev. 2012, 112, 3193. - PubMed

    1. For examples of their occurrence in electronic organic materials, see:

    2. van Dijken A.; Bastiaansen J. J. A. M.; Kiggen N. M. M.; Langeveld B. M. W.; Rothe C.; Monkman A.; Bach I.; Stössel P.; Brunner K. J. Am. Chem. Soc. 2004, 126, 7718. - PubMed
    3. Wu Y.; Li Y.; Gardner S.; Ong B. S. J. Am. Chem. Soc. 2005, 127, 614. - PubMed
    4. Boudreault P.-L. T.; Wakim S.; Blouin N.; Simard M.; Tessier C.; Tao Y.; Leclerc M. J. Am. Chem. Soc. 2007, 129, 9125. - PubMed
    5. Wang C.; Dong H.; Hu W.; Liu Y.; Zhu D. Chem. Rev. 2011, 112, 2208. - PubMed
    1. Stokes B. J.; Dong H.; Leslie B. E.; Pumphrey A. L.; Driver T. G. J. Am. Chem. Soc. 2007, 129, 7500. - PubMed
    2. Shen M.; Leslie B. E.; Driver T. G. Angew. Chem., Int. Ed. 2008, 47, 5056. - PubMed
    3. Stokes B. J.; Jovanović B.; Dong H.; Richert K. J.; Riell R. D.; Driver T. G. J. Org. Chem. 2009, 74, 3225. - PMC - PubMed
    4. Pumphrey A. L.; Dong H.; Driver T. G. Angew. Chem., Int. Ed. 2012, 51, 5920. - PMC - PubMed

    1. For reviews on the preparation of vinyl or aryl azides, see:

    2. L’abbé G. Angew. Chem., Int. Ed. 1975, 14, 775.
    3. Scriven E. F. V.; Turnbull K. Chem. Rev. 1988, 88, 297.
    4. Bräse S.; Gil C.; Knepper K.; Zimmermann V. Angew. Chem., Int. Ed. 2005, 44, 5188. - PubMed

    1. For a discussion of the importance of step economy in organic synthesis, see:

    2. Wender P. A.; Verma V. A.; Paxton T. J.; Pillow T. H. Acc. Chem. Res. 2008, 41, 40. - PubMed
    3. Newhouse T.; Baran P. S.; Hoffmann R. W. Chem. Soc. Rev. 2009, 38, 3010. - PMC - PubMed

Publication types