Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 10, Pages 1921-1925Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7qo00420f
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Funding
- National Natural Science Foundation of China [21172081, 21372090]
- Natural Science Foundation of Guangdong Province [S2013020013091]
- City of Guangzhou Science and Technology Plan Projects [201510010054]
- Graduate Student Research and Innovation Foundation of South China Normal University [2016lkxm30]
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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.
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