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Issue 44, 2016
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Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation

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Abstract

Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C–C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.

Graphical abstract: Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation

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Publication details

The article was received on 08 Sep 2016, accepted on 15 Oct 2016 and first published on 15 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01979J
Citation: Org. Biomol. Chem., 2016,14, 10511-10515
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    Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation

    S. Zhang and Z. Yu, Org. Biomol. Chem., 2016, 14, 10511
    DOI: 10.1039/C6OB01979J

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