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Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C–C or C–N bond cleavage

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Abstract

Rh(III)-Catalyzed C–C/C–O bond formation between cyclic 2-diazo-1,3-diketones and salicylamides with additive-controlled chemoselectivity is described. The reaction proceeded under mild reaction conditions and exhibited good functional group tolerance and scalability. 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones were obtained in moderate to excellent yields (55–90%) through a tandem N–H activation/C–C cleavage/etherification process when AgNTf2 was used as the additive, whereas utilizing Cu(OAc)2 afforded isocoumarins in good yields (60–86%) via a C–H activation/C–N cleavage/lactonization pathway.

Graphical abstract: Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C–C or C–N bond cleavage

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Publication details

The article was received on 05 Oct 2017, accepted on 12 Dec 2017 and first published on 13 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ03799F
Citation: New J. Chem., 2018, Advance Article
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    Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C–C or C–N bond cleavage

    Y. Zuo, X. He, Y. Ning, L. Zhang, Y. Wu and Y. Shang, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ03799F

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