Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 10241-10247Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01443
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- Ministry of Science and Technology of the Republic of China [MOST 103-2113M-003-008-MY3]
- National Taiwan Normal University (NTNU) [103-07-C]
- MOST
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The copper-catalyzed reaction of aryl aldehydes with 2-iodobenzylcyanides afforded 2-aryl-3-cyanobenzofurans in isolated yields of up to 74% in a cascade manner, which involves Knoevenagel condensation, aryl hydroxylation, oxa-Michael addition, and aromatization reactions. Conversely, 2-halo benzaldehydes as reacting partners with 2-iodobenzylcyanide regioselectively furnished dibenzo[b,f]oxepine-10-carbonitrile derivatives up to 85% isolated yields via tandem Knoevenagel condensation, aryl hydroxylation, and Ullmann coupling reactions.
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