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Palladium(II)-catalyzed synthesis of functionalized indenes from o-alkynylbenzylidene ketones.
J Org Chem. 2011 Mar 04; 76(5):1491-4.JO

Abstract

An efficient method for the synthesis of functionalized indenes from o-alkynylbenzylidene ketones under palladium(II) catalysis was developed. The reaction is initiated by trans-nucleopalladation of alkynes, followed by conjugate addition and quenched by protonolysis of the carbon-palladium bond. With acetate and halide ions as nucleophiles, 3-acetoxy- and 3-halogen-substituted indenes could be obtained in high yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou F
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Han X
No affiliation info available
Lu X
No affiliation info available

MeSH

CatalysisIndenesKetonesMolecular StructureOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21250715

Citation

Zhou, Feng, et al. "Palladium(II)-catalyzed Synthesis of Functionalized Indenes From O-alkynylbenzylidene Ketones." The Journal of Organic Chemistry, vol. 76, no. 5, 2011, pp. 1491-4.
Zhou F, Han X, Lu X. Palladium(II)-catalyzed synthesis of functionalized indenes from o-alkynylbenzylidene ketones. J Org Chem. 2011;76(5):1491-4.
Zhou, F., Han, X., & Lu, X. (2011). Palladium(II)-catalyzed synthesis of functionalized indenes from o-alkynylbenzylidene ketones. The Journal of Organic Chemistry, 76(5), 1491-4. https://doi.org/10.1021/jo1023574
Zhou F, Han X, Lu X. Palladium(II)-catalyzed Synthesis of Functionalized Indenes From O-alkynylbenzylidene Ketones. J Org Chem. 2011 Mar 4;76(5):1491-4. PubMed PMID: 21250715.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(II)-catalyzed synthesis of functionalized indenes from o-alkynylbenzylidene ketones. AU - Zhou,Feng, AU - Han,Xiuling, AU - Lu,Xiyan, Y1 - 2011/01/20/ PY - 2011/1/22/entrez PY - 2011/1/22/pubmed PY - 2011/6/8/medline SP - 1491 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 5 N2 - An efficient method for the synthesis of functionalized indenes from o-alkynylbenzylidene ketones under palladium(II) catalysis was developed. The reaction is initiated by trans-nucleopalladation of alkynes, followed by conjugate addition and quenched by protonolysis of the carbon-palladium bond. With acetate and halide ions as nucleophiles, 3-acetoxy- and 3-halogen-substituted indenes could be obtained in high yields. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21250715/Palladium_II__catalyzed_synthesis_of_functionalized_indenes_from_o_alkynylbenzylidene_ketones_ L2 - https://doi.org/10.1021/jo1023574 DB - PRIME DP - Unbound Medicine ER -