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Issue 10, 2017
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Platinum-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with sodium arylsulfinates

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Abstract

A new efficient platinum-catalyzed ring-opening reaction of oxabicyclic alkenes with a wide range of sodium arylsulfinates was developed, affording the desired products 3 or 4 in good to excellent yields under mild conditions. This protocol provides a new low-cost, viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ols 3 and 2-aryl-naphthalenes 4 with good functional group tolerance. To the best of our knowledge, it represents the first example in the ring-opening reactions of oxabicyclic alkenes with sodium arylsulfinates via a platinum catalyst and desulfonylation using the Pt catalyst. In addition, a plausible mechanism for the ring-opening reaction was also proposed.

Graphical abstract: Platinum-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with sodium arylsulfinates

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Publication details

The article was received on 28 May 2017, accepted on 21 Jun 2017 and first published on 22 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00420F
Citation: Org. Chem. Front., 2017,4, 1921-1925
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    Platinum-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with sodium arylsulfinates

    R. Wu, W. Yang, W. Chen and D. Yang, Org. Chem. Front., 2017, 4, 1921
    DOI: 10.1039/C7QO00420F

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