Journal
CHEMICAL SCIENCE
Volume 7, Issue 8, Pages 5206-5211Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc00798h
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Funding
- JSPS KAKENHI [23790017, 24390005, 25460018]
- MEXT
- Hoansha foundation
- [15J06024]
- Grants-in-Aid for Scientific Research [16K08164, 23790017, 15J06024, 25460018, 16K18843] Funding Source: KAKEN
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We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics.
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