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Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids.
J Org Chem. 2008 Jan 04; 73(1):320-2.JO

Abstract

Treatment of fluorapatite (prepared by incorporating basic species F(-) in apatite in situ by coprecipitation) with an aqueous solution of RhCl(3) resulted in rhodium-exchanged fluorapatite catalyst (RhFAP), which successfully promoted cross coupling of Baylis-Hillman adducts with arylboronic acids to yield trisubstituted olefins. A variety of arylboronic acids and Baylis-Hillman adducts were converted to the corresponding trisubstituted olefins, demonstrating the versatility of the reaction. The reaction is highly stereoselective. RhFAP was recovered quantitatively by simple filtration and reused with almost consistent activity.

Authors+Show Affiliations

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India. mlakshmi@iict.res.inNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18072787

Citation

Kantam, M Lakshmi, et al. "Rhodium Fluorapatite Catalyst for the Synthesis of Trisubstituted Olefins Via Cross Coupling of Baylis-Hillman Adducts and Arylboronic Acids." The Journal of Organic Chemistry, vol. 73, no. 1, 2008, pp. 320-2.
Kantam ML, Kumar KB, Sreedhar B. Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids. J Org Chem. 2008;73(1):320-2.
Kantam, M. L., Kumar, K. B., & Sreedhar, B. (2008). Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids. The Journal of Organic Chemistry, 73(1), 320-2.
Kantam ML, Kumar KB, Sreedhar B. Rhodium Fluorapatite Catalyst for the Synthesis of Trisubstituted Olefins Via Cross Coupling of Baylis-Hillman Adducts and Arylboronic Acids. J Org Chem. 2008 Jan 4;73(1):320-2. PubMed PMID: 18072787.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids. AU - Kantam,M Lakshmi, AU - Kumar,K B Shiva, AU - Sreedhar,B, Y1 - 2007/12/12/ PY - 2007/12/13/pubmed PY - 2008/3/20/medline PY - 2007/12/13/entrez SP - 320 EP - 2 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 1 N2 - Treatment of fluorapatite (prepared by incorporating basic species F(-) in apatite in situ by coprecipitation) with an aqueous solution of RhCl(3) resulted in rhodium-exchanged fluorapatite catalyst (RhFAP), which successfully promoted cross coupling of Baylis-Hillman adducts with arylboronic acids to yield trisubstituted olefins. A variety of arylboronic acids and Baylis-Hillman adducts were converted to the corresponding trisubstituted olefins, demonstrating the versatility of the reaction. The reaction is highly stereoselective. RhFAP was recovered quantitatively by simple filtration and reused with almost consistent activity. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18072787/Rhodium_fluorapatite_catalyst_for_the_synthesis_of_trisubstituted_olefins_via_cross_coupling_of_Baylis_Hillman_adducts_and_arylboronic_acids_ L2 - https://doi.org/10.1021/jo701982m DB - PRIME DP - Unbound Medicine ER -