Abstract
A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.
| Original language | English |
|---|---|
| Pages (from-to) | 1668-1672 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 57 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2018 Feb 5 |
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Keywords
- Wittig reactions
- chemoselectivity
- diversity-oriented synthesis
- multicomponent reactions
- organophosphonium salts
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
Cite this
Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction. / Yang, Shu Mei; Wang, Chein Yi; Lin, Chun Kai; Karanam, Praneeth; Reddy, Ganapuram Madhusudhan; Tsai, Yi Ling; Lin, Wen-Wei.
In: Angewandte Chemie - International Edition, Vol. 57, No. 6, 05.02.2018, p. 1668-1672.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diversity-Oriented Synthesis of Furo[3,2-c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction
AU - Yang, Shu Mei
AU - Wang, Chein Yi
AU - Lin, Chun Kai
AU - Karanam, Praneeth
AU - Reddy, Ganapuram Madhusudhan
AU - Tsai, Yi Ling
AU - Lin, Wen-Wei
PY - 2018/2/5
Y1 - 2018/2/5
N2 - A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.
AB - A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.
KW - Wittig reactions
KW - chemoselectivity
KW - diversity-oriented synthesis
KW - multicomponent reactions
KW - organophosphonium salts
UR - http://www.scopus.com/inward/record.url?scp=85041031446&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85041031446&partnerID=8YFLogxK
U2 - 10.1002/anie.201711524
DO - 10.1002/anie.201711524
M3 - Article
AN - SCOPUS:85041031446
VL - 57
SP - 1668
EP - 1672
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 6
ER -