One‐pot Synthesis of Alkynylated Coumarins via Rhodium‐Catalyzed Annulation of Aryl Thiocarbamates with 1,3‐Diynes or Terminal Alkynes
A convenient and selective synthesis of alkynylated coumarins from various aryl thiocarbamates and 1,3‐diynes or terminal alkynes via rhodium‐catalyzed C−H bond activation has been developed. In this transformation, both symmetrical and asymmetrical 1,3‐diynes could be applicable, obtaining various...
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Published in | Advanced synthesis & catalysis Vol. 360; no. 7; pp. 1328 - 1333 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
03.04.2018
Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | A convenient and selective synthesis of alkynylated coumarins from various aryl thiocarbamates and 1,3‐diynes or terminal alkynes via rhodium‐catalyzed C−H bond activation has been developed. In this transformation, both symmetrical and asymmetrical 1,3‐diynes could be applicable, obtaining various 3‐alkynylated coumarins in moderate to excellent yields. When the substituent is aryl group, the resulting compounds were found to exhibit intense fluorescence in the range of 412–443 nm with quantum yield of up to 0.57 in CH2Cl2. Moreover, the internal alkynes were readily converted to 1,2‐dione, olefins, alkanes, and bisheterocycles under certain conditions. |
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ISSN: | 1615-4150 1615-4169 |
DOI: | 10.1002/adsc.201701388 |