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Higashimae S, Tamai T, Nomoto A, et al. Selective Thiolative Lactonization of Internal Alkynes Bearing a Hydroxyl Group with Carbon Monoxide and Organic Disulfides Catalyzed by Transition-Metal Complexes. J Org Chem. 2015;80(14):7126-33doi: 10.1021/acs.joc.5b00977.
Higashimae, S., Tamai, T., Nomoto, A., & Ogawa, A. (2015). Selective Thiolative Lactonization of Internal Alkynes Bearing a Hydroxyl Group with Carbon Monoxide and Organic Disulfides Catalyzed by Transition-Metal Complexes. The Journal of organic chemistry, 80(14), 7126-33. https://doi.org/10.1021/acs.joc.5b00977
Higashimae, Shinya, et al. "Selective Thiolative Lactonization of Internal Alkynes Bearing a Hydroxyl Group with Carbon Monoxide and Organic Disulfides Catalyzed by Transition-Metal Complexes." The Journal of organic chemistry vol. 80,14 (2015): 7126-33. doi: https://doi.org/10.1021/acs.joc.5b00977
Higashimae S, Tamai T, Nomoto A, Ogawa A. Selective Thiolative Lactonization of Internal Alkynes Bearing a Hydroxyl Group with Carbon Monoxide and Organic Disulfides Catalyzed by Transition-Metal Complexes. J Org Chem. 2015 Jul 17;80(14):7126-33. doi: 10.1021/acs.joc.5b00977. Epub 2015 Jul 07. PMID: 26072971.
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J Org Chem. 2015 Jul 17;80(14):7126-33. doi: 10.1021/acs.joc.5b00977. Epub 2015 Jul 07.

Selective Thiolative Lactonization of Internal Alkynes Bearing a Hydroxyl Group with Carbon Monoxide and Organic Disulfides Catalyzed by Transition-Metal Complexes.

The Journal of organic chemistry

Shinya Higashimae, Taichi Tamai, Akihiro Nomoto, Akiya Ogawa

Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.

PMID: 26072971 DOI: 10.1021/acs.joc.5b00977

Abstract

Although many transition-metal catalysts are ineffective for the addition and carbonylative addition of organic disulfides to internal alkynes, dicobalt octacarbonyl and palladium complexes such as Pd(PPh3)4 and Pd(OAc)2 were found to exhibit excellent catalytic activity for the thiolative lactonization of internal alkynes bearing a hydroxyl group. In the presence of the cobalt or palladium catalyst, internal alkynes bearing a hydroxy group, such as homopropargyl alcohol derivatives, successfully undergo thiolative carbonylation with carbon monoxide and an organic disulfide regio- and stereoselectively to afford the corresponding thio group bearing-lactones in good yields. In the Co-catalyzed reaction, the cobalt-alkyne complex from dicobalt octacarbonyl and internal alkyne acts as a key species, making it possible to attain thiolative lactonization of internal alkynes with a hydroxyl group. In the Pd-catalyzed reaction, the coordination of the hydroxy group to the palladium catalyst plays an important role for the thiolative lactonization.

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