Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 44, Pages 10511-10515Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01979j
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Funding
- National Natural Science Foundation of China [21472068, 21202062]
- Natural Science Foundation of Jiangsu Province [BK2012108]
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Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of beta-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/alpha-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce alpha-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.
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