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Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds.
Org Lett. 2013 Apr 05; 15(7):1476-9.OL

Abstract

A novel rhodium(III)-catalyzed direct functionalization of the ortho-C-H bond of aromatic ketone derivatives and an intramolecular cyclization sequence produced indene derivatives in moderate to good yields. This cascade cyclization involves a conjugate addition of α,β-unsaturated ketone and subsequent aldol condensation. The reaction occurred efficiently in the presence of water and under an atmosphere of air.

Authors+Show Affiliations

Department of Chemistry, McGill University, Montreal, QC H3A 2K6, Canada.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23470191

Citation

Shi, Xian-Ying, and Chao-Jun Li. "Synthesis of Indene Frameworks Via Rhodium-catalyzed Cascade Cyclization of Aromatic Ketone and Unsaturated Carbonyl Compounds." Organic Letters, vol. 15, no. 7, 2013, pp. 1476-9.
Shi XY, Li CJ. Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds. Org Lett. 2013;15(7):1476-9.
Shi, X. Y., & Li, C. J. (2013). Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds. Organic Letters, 15(7), 1476-9. https://doi.org/10.1021/ol400198q
Shi XY, Li CJ. Synthesis of Indene Frameworks Via Rhodium-catalyzed Cascade Cyclization of Aromatic Ketone and Unsaturated Carbonyl Compounds. Org Lett. 2013 Apr 5;15(7):1476-9. PubMed PMID: 23470191.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds. AU - Shi,Xian-Ying, AU - Li,Chao-Jun, Y1 - 2013/03/07/ PY - 2013/3/9/entrez PY - 2013/3/9/pubmed PY - 2013/9/24/medline SP - 1476 EP - 9 JF - Organic letters JO - Org Lett VL - 15 IS - 7 N2 - A novel rhodium(III)-catalyzed direct functionalization of the ortho-C-H bond of aromatic ketone derivatives and an intramolecular cyclization sequence produced indene derivatives in moderate to good yields. This cascade cyclization involves a conjugate addition of α,β-unsaturated ketone and subsequent aldol condensation. The reaction occurred efficiently in the presence of water and under an atmosphere of air. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23470191/Synthesis_of_indene_frameworks_via_rhodium_catalyzed_cascade_cyclization_of_aromatic_ketone_and_unsaturated_carbonyl_compounds_ L2 - https://doi.org/10.1021/ol400198q DB - PRIME DP - Unbound Medicine ER -