Journal
SYNLETT
Volume 26, Issue 11, Pages 1578-1580Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1380686
Keywords
iridium; palladium; catalysis; C-H activation; Suzuki coupling; synthesis; methodology; functionalization
Categories
Funding
- National Science Foundation
- Department of Energy
- PRESTO, Japan Science and Technology Agency
- Mazume Research Encouragement Prize in Kyoto University
- Grants-in-Aid for Scientific Research [15J09809, 26288093] Funding Source: KAKEN
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1149096] Funding Source: National Science Foundation
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Exhaustive borylation of azulene with excess bis(pinacolato)-diboron (B(2)pin(2)) under conditions that promote equilibration of the borylated azulenes provides a convenient one-step synthesis of 1,3,5,7-tetra(Bpin)azulene as the major product. The Bpin substituents at positions 1 and 3 can be conveniently removed from 1,3,5,7-tetra-(Bpin)azulene by treatment with trifluoroacetic acid at room temperature to give 5,7-di(Bpin)azulene. The utility of 5,7-di(Bpin)azulene as a synthetic precursor to 5,7-disubstituted azulenes that are otherwise difficult to access is demonstrated by Suzuki coupling to give the previously unknown 5,7-diphenylazulene.
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