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Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations.
J Org Chem. 2009 Jan 02; 74(1):182-7.JO

Abstract

Described herein are the scope and limitations using Tp*Rh(PPh(3))(2) as a catalyst for alkyne hydrothiolation with alkyl thiols. In general, catalytic hydrothiolation proceeds in high yields and with high regioselectivity for a wide range of alkynes and thiols. A variety of functional groups were well-tolerated, including nitriles, amines, halogens, ethers, esters and silanes, although strongly coordinating groups were found to be incompatible with hydrothiolation. Both sterically encumbered alkynes and thiols were successful in hydrothiolation. Electron rich alkynes react more rapidly than electron deficient alkynes. Overall, this hydrothiolation protocol provides convenient access to a variety of functionalized branched alkyl vinyl sulfides.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang J
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada.
Sabarre A
No affiliation info available
Fraser LR
No affiliation info available
Patrick BO
No affiliation info available
Love JA
No affiliation info available

MeSH

AlkynesCatalysisCrystallography, X-RayModels, MolecularMolecular StructureOrganometallic CompoundsRhodiumStereoisomerismSulfhydryl CompoundsVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

19053611

Citation

Yang, Jun, et al. "Synthesis of 1,1-disubstituted Alkyl Vinyl Sulfides Via Rhodium-catalyzed Alkyne Hydrothiolation: Scope and Limitations." The Journal of Organic Chemistry, vol. 74, no. 1, 2009, pp. 182-7.
Yang J, Sabarre A, Fraser LR, et al. Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations. J Org Chem. 2009;74(1):182-7.
Yang, J., Sabarre, A., Fraser, L. R., Patrick, B. O., & Love, J. A. (2009). Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations. The Journal of Organic Chemistry, 74(1), 182-7. https://doi.org/10.1021/jo801644s
Yang J, et al. Synthesis of 1,1-disubstituted Alkyl Vinyl Sulfides Via Rhodium-catalyzed Alkyne Hydrothiolation: Scope and Limitations. J Org Chem. 2009 Jan 2;74(1):182-7. PubMed PMID: 19053611.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations. AU - Yang,Jun, AU - Sabarre,Anthony, AU - Fraser,Lauren R, AU - Patrick,Brian O, AU - Love,Jennifer A, PY - 2008/12/5/pubmed PY - 2009/2/13/medline PY - 2008/12/5/entrez SP - 182 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 1 N2 - Described herein are the scope and limitations using Tp*Rh(PPh(3))(2) as a catalyst for alkyne hydrothiolation with alkyl thiols. In general, catalytic hydrothiolation proceeds in high yields and with high regioselectivity for a wide range of alkynes and thiols. A variety of functional groups were well-tolerated, including nitriles, amines, halogens, ethers, esters and silanes, although strongly coordinating groups were found to be incompatible with hydrothiolation. Both sterically encumbered alkynes and thiols were successful in hydrothiolation. Electron rich alkynes react more rapidly than electron deficient alkynes. Overall, this hydrothiolation protocol provides convenient access to a variety of functionalized branched alkyl vinyl sulfides. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19053611/Synthesis_of_11_disubstituted_alkyl_vinyl_sulfides_via_rhodium_catalyzed_alkyne_hydrothiolation:_scope_and_limitations_ L2 - https://doi.org/10.1021/jo801644s DB - PRIME DP - Unbound Medicine ER -