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A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones.
Org Lett. 2008 Jul 03; 10(13):2633-6.OL

Abstract

A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or "anti-Wacker"-type oxidative addition to the Pd(0) catalyst.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tsukamoto H
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan. hirokazu@mail.pharm.tohoku.ac.jp
Kondo Y
No affiliation info available

MeSH

AldehydesAlkadienesAlkylationCatalysisCyclizationMolecular StructureOxidation-ReductionPalladium

Pub Type(s)

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

Language

eng

PubMed ID

18510328

Citation

Tsukamoto, Hirokazu, and Yoshinori Kondo. "A New Five-membered Ring Forming Process Based On Palladium(0)-catalyzed Arylative Cyclization of Allenyl Enones." Organic Letters, vol. 10, no. 13, 2008, pp. 2633-6.
Tsukamoto H, Kondo Y. A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones. Org Lett. 2008;10(13):2633-6.
Tsukamoto, H., & Kondo, Y. (2008). A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones. Organic Letters, 10(13), 2633-6. https://doi.org/10.1021/ol800509z
Tsukamoto H, Kondo Y. A New Five-membered Ring Forming Process Based On Palladium(0)-catalyzed Arylative Cyclization of Allenyl Enones. Org Lett. 2008 Jul 3;10(13):2633-6. PubMed PMID: 18510328.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones. AU - Tsukamoto,Hirokazu, AU - Kondo,Yoshinori, Y1 - 2008/05/30/ PY - 2008/5/31/pubmed PY - 2008/9/17/medline PY - 2008/5/31/entrez SP - 2633 EP - 6 JF - Organic letters JO - Org Lett VL - 10 IS - 13 N2 - A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or "anti-Wacker"-type oxidative addition to the Pd(0) catalyst. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18510328/A_new_five_membered_ring_forming_process_based_on_palladium_0__catalyzed_arylative_cyclization_of_allenyl_enones_ L2 - https://doi.org/10.1021/ol800509z DB - PRIME DP - Unbound Medicine ER -