Journal
ORGANIC LETTERS
Volume 23, Issue 14, Pages 5317-5322Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01532
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Funding
- National Natural Science Foundation of China [21676076, 21878071, 21971060]
- Hu-Xiang High Talent Project in Hunan Province [2018RS3042]
- Recruitment Program for Foreign Experts of China [WQ20164300353]
- Natural Science Foundation of Changsha [kq2004008]
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A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes was developed for the synthesis of (E)-olefins. The method provides unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes with high yields and selectivity. Some products exhibit good photoluminescence quantum yields.
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E ,3E)- 1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
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