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
. 2012 Jan 11;134(1):111-4.
doi: 10.1021/ja2095393. Epub 2011 Dec 9.

Palladium-catalyzed C3-benzylation of indoles

Ye Zhu  1 , Viresh H Rawal
Affiliations

Palladium-catalyzed C3-benzylation of indoles

Ye Zhu et al. J Am Chem Soc. .

Abstract

A general method for regioselective C3-benzylation of indoles has been developed. Various 3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Pd-catalyzed Indole Benzylation
Scheme 2
Scheme 2
Competition studies a a Reaction conditions are the same as in Table 3.
Scheme 3
Scheme 3
Proposed reaction mechanism a
See this image and copyright information in PMC

References

    1. Cacchi S, Fabrizi G. Chem. Rev. 2005;105:2873. - PubMed
    2. Chem. Rev. 2011;111:PR215. Update 1: - PubMed
    3. Joucla L, Djakovitch L. Adv. Synth. Catal. 2009;351:673.
    4. Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009;48:9608. - PubMed
    5. Bartoli G, Bencivenni G, Dalpozzo R. Chem. Soc. Rev. 2010;39:4449. - PubMed

    1. For selected examples of Pd-catalyzed allylation reaction of 3-unsubstituted indoles: Bandini M, Melloni A, Umani-Ronchi A. Org. Lett. 2004;6:3199. Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc. 2005;127:4592. Bandini M, Melloni A, Piccinelli F, Sinisi R, Tommasi S, Umani-Ronchi A. J. Am. Chem. Soc. 2006;128:1424. 3-Substituted indoles: Trost BM, Quancard J. J. Am. Chem. Soc. 2006;128:6314. Kagawa N, Malerich JP, Rawal VH. Org. Lett. 2008;10:2381.

    1. For examples of alkylation of indolyl anion using alkyl halide: Hoshino T. Liebigs Ann. Chem. 1933;500:35. Nakazaki M. Bull. Chem. Soc. Jpn. 1959;32:838. Reactions between indoles and o-halomethyl phenol/aniline: Spande TF, Wilchek M, Witkop B. J. Am. Chem. Soc. 1968;90:3256. May JA, Zeidan RK, Stoltz BM. Tetrahedron Lett. 2003;44:1203.

    1. For selected examples using indolenines as intermediates in syntheses: Robinson R, Suginome H. J. Chem. Soc. 1932:298. Woodward RB, Cava MP, Ollis WD, Hunger A, Daeniker HU, Schenker K. J. Am. Chem. Soc. 1954;76:4749. Stork G, Dolfini JE. J. Am. Chem. Soc. 1963;85:2872. He F, Bo Y, Altom JD, Corey EJ. J. Am. Chem. Soc. 1999;121:6771. Kozmin SA, Iwama T, Huang Y, Rawal VH. J. Am. Chem. Soc. 2002;124:4628.

    1. Numata A, Takahashi C, Ito Y, Takada T, Kawai K, Usami Y, Matsumura E, Imachi M, Ito T, Hasegawa T. Tetrahedron Lett. 1993;34:2355.
    2. Verbitski SM, Mayne CL, Davis RA, Concepcion GP, Ireland CM. J. Org. Chem. 2002;67:7124. - PubMed
    3. Yu S, Qin D, Shangary S, Chen J, Wang G, Ding K, McEachern D, Qiu S, Nikolovska-Coleska Z, Miller R, Kang S, Yang D, Wang S. J. Med. Chem. 2009;52:7970. - PMC - PubMed

Publication types