Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 10241-10247 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2018 Sep 7 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives. / Villuri, Bharath Kumar; Ichake, Sachin S.; Reddy, Sabbasani Rajasekhara; Kavala, Veerababurao; Bandi, Vijayalakshmi; Kuo, Chun Wei; Yao, Ching Fa.
In: Journal of Organic Chemistry, Vol. 83, No. 17, 07.09.2018, p. 10241-10247.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives
AU - Villuri, Bharath Kumar
AU - Ichake, Sachin S.
AU - Reddy, Sabbasani Rajasekhara
AU - Kavala, Veerababurao
AU - Bandi, Vijayalakshmi
AU - Kuo, Chun Wei
AU - Yao, Ching Fa
PY - 2018/9/7
Y1 - 2018/9/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85050026056&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85050026056&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01443
DO - 10.1021/acs.joc.8b01443
M3 - Article
VL - 83
SP - 10241
EP - 10247
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -