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Efficient synthesis of 3-iodoindenes via Lewis-acid catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols.
J Org Chem. 2008 May 16; 73(10):3958-60.JO

Abstract

A convenient BF(3).Et(2)O-catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols is reported. The present reaction provides an efficient protocol to 3-iodo-1(H)-indene derivatives in good to high yields under mild conditions. Further, the iodoindene derivatives are valuable synthetic building blocks for elaboration of molecular complexity, such as in the construction of multiaryl substituted indenes by Suzuki coupling reaction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou X
Institute of Medicinal Chemistry, Department of Chemistry, East China Normal University, Shanghai, PR China.
Zhang H
No affiliation info available
Xie X
No affiliation info available
Li Y
No affiliation info available

MeSH

AcidsCatalysisCyclizationHydrocarbons, IodinatedIndenesMolecular StructurePropanolsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18419158

Citation

Zhou, Xiaobo, et al. "Efficient Synthesis of 3-iodoindenes Via Lewis-acid Catalyzed Friedel-Crafts Cyclization of Iodinated Allylic Alcohols." The Journal of Organic Chemistry, vol. 73, no. 10, 2008, pp. 3958-60.
Zhou X, Zhang H, Xie X, et al. Efficient synthesis of 3-iodoindenes via Lewis-acid catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols. J Org Chem. 2008;73(10):3958-60.
Zhou, X., Zhang, H., Xie, X., & Li, Y. (2008). Efficient synthesis of 3-iodoindenes via Lewis-acid catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols. The Journal of Organic Chemistry, 73(10), 3958-60. https://doi.org/10.1021/jo800232p
Zhou X, et al. Efficient Synthesis of 3-iodoindenes Via Lewis-acid Catalyzed Friedel-Crafts Cyclization of Iodinated Allylic Alcohols. J Org Chem. 2008 May 16;73(10):3958-60. PubMed PMID: 18419158.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient synthesis of 3-iodoindenes via Lewis-acid catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols. AU - Zhou,Xiaobo, AU - Zhang,Huimin, AU - Xie,Xin, AU - Li,Yanzhong, Y1 - 2008/04/18/ PY - 2008/4/19/pubmed PY - 2008/8/14/medline PY - 2008/4/19/entrez SP - 3958 EP - 60 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 10 N2 - A convenient BF(3).Et(2)O-catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols is reported. The present reaction provides an efficient protocol to 3-iodo-1(H)-indene derivatives in good to high yields under mild conditions. Further, the iodoindene derivatives are valuable synthetic building blocks for elaboration of molecular complexity, such as in the construction of multiaryl substituted indenes by Suzuki coupling reaction. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18419158/Efficient_synthesis_of_3_iodoindenes_via_Lewis_acid_catalyzed_Friedel_Crafts_cyclization_of_iodinated_allylic_alcohols_ DB - PRIME DP - Unbound Medicine ER -