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Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling.
J Am Chem Soc. 2012 Feb 15; 134(6):2906-9.JA

Abstract

A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.

Authors+Show Affiliations

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

22296656

Citation

Hooper, Joel F., et al. "Aryl Methyl Sulfides as Substrates for Rhodium-catalyzed Alkyne Carbothiolation: Arene Functionalization With Activating Group Recycling." Journal of the American Chemical Society, vol. 134, no. 6, 2012, pp. 2906-9.
Hooper JF, Chaplin AB, González-Rodríguez C, et al. Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. J Am Chem Soc. 2012;134(6):2906-9.
Hooper, J. F., Chaplin, A. B., González-Rodríguez, C., Thompson, A. L., Weller, A. S., & Willis, M. C. (2012). Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. Journal of the American Chemical Society, 134(6), 2906-9. https://doi.org/10.1021/ja2108992
Hooper JF, et al. Aryl Methyl Sulfides as Substrates for Rhodium-catalyzed Alkyne Carbothiolation: Arene Functionalization With Activating Group Recycling. J Am Chem Soc. 2012 Feb 15;134(6):2906-9. PubMed PMID: 22296656.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. AU - Hooper,Joel F, AU - Chaplin,Adrian B, AU - González-Rodríguez,Carlos, AU - Thompson,Amber L, AU - Weller,Andrew S, AU - Willis,Michael C, Y1 - 2012/02/07/ PY - 2012/2/3/entrez PY - 2012/2/3/pubmed PY - 2012/7/20/medline SP - 2906 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 6 N2 - A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22296656/Aryl_methyl_sulfides_as_substrates_for_rhodium_catalyzed_alkyne_carbothiolation:_arene_functionalization_with_activating_group_recycling_ L2 - https://doi.org/10.1021/ja2108992 DB - PRIME DP - Unbound Medicine ER -