期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 2, 页码 532-539出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000836
关键词
2-Aryloxybenzaldehyde; 2-(arylthio)benzaldehyde; xanthylium ion; hydride transfer; chemoselective reduction; 9H-xanthene; reductive cyclization
资金
- Council of Scientific and Industrial Research, India [02(0346)/19/EMR-II]
- UGC, New Delhi
- CSIR, New Delhi
Readily accessible 2-aryloxybenzaldehydes and 2-(arylthio)benzaldehydes can undergo a sequence of reactions to form a wide variety of unsubstituted 9H-xanthenes and thioxanthenes in high yields when heated with a Lewis acid in diisopropyl ether. This reductive cyclization method is compatible with several important functional groups and allows for the selective reductive cyclization of the more electron-rich aryl ring of a 2,6-bis(aryloxy)benzaldehyde. The key feature of this transformation is the chemoselective reduction of a transient xanthylium ion in the presence of an aldehydic group via intermolecular hydride transfer from diisopropyl ether (solvent).
Readily accessible 2-aryloxybenzaldehydes and 2-(arylthio)benzaldehydes undergo a sequence of reactions leading to a wide variety of unsubstituted 9H-xanthenes and thioxanthenes in high yields when heated with a Lewis acid in diisopropyl ether. This reductive cyclization method is compatible with several important functional groups. The method is also applicable for the selective reductive cyclization of the more electron-rich aryl ring of a 2,6-bis(aryloxy)benzaldehyde. The key feature of this transformation is the chemoselective reduction of a transient xanthylium ion in the presence of aldehydic group via intermolecular hydride transfer from diisopropyl ether (solvent).
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