Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 7, Issue 7, Pages 1644-1651Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201200132
Keywords
annulation; arenes; boron; cross-coupling; palladium
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [16GS0209]
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [16GS0209, 10J05440] Funding Source: KAKEN
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(Z)-1,2-Diaryl-1,2-bis(pinacolatoboryl)ethenes underwent double-cross-coupling reactions with 1-bromo-2-[(Z)-2-bromoethenyl]arenes in the presence of [Pd(PPh3)4] as a catalyst and 3?M aqueous Cs2CO3 as a base in THF at 80?degrees C. The double-coupling reaction gave multisubstituted naphthalenes in good to high yields. Annulation of 1,2-bis(pinacolatoboryl)arenes with bromo(bromoethenyl)arenes in the presence of a catalyst system that consisted of [Pd2(dba)3] (dba=dibenzylideneacetone) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) under the same conditions produced fused phenanthrenes in good to high yields. The first annulation coupling occurred regiospecifically at the bromoethenyl moiety. This procedure is applicable to the facile synthesis of polysubstituted anthracenes, benzothiophenes, and dibenzoanthracenes through a double annulation pathway by using the corresponding dibromobis[(Z)-2-bromoethenyl]benzenes as diboryl coupling partners.
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