• Journal of the Korean Chemical Society
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• v.61 no.3
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• pp.125-128
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• 2017

• Bulletin of the Korean Chemical Society
• /
• v.17 no.2
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• pp.113-114
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• 1996

• Bulletin of the Korean Chemical Society
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• v.16 no.9
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• pp.799-801
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• 1995

• Journal of the Korean Chemical Society
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• v.50 no.5
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• pp.369-373
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• 2006

Arylation reactions of styrene catalyzed by Pd(CF3CO2)2-sulfides and Pd(CF3CO2)2-phosphines were investigated. The yield of trans-stilbene, the main product, increased as the basicity of the substituents on the aryl groups of the phosphines increased and the steric hindrance of the substituents decreased. The mechanism of the aryl migration of arylphosphines to styrene is proposed to involve the electrophilic attack of Pd to the phenyl group on the phosphines. The phosphine systems were found to be more effective than the sulfide ones.

• Bulletin of the Korean Chemical Society
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• v.18 no.2
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• pp.218-221
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• 1997

When phenylation of styrene was carried out in the presence of Pd(OAc)2 and PPh3 in benzene, trans-stilbene was obtained in good yield (566%) with high selectivity (98%) under mild condition (55 ℃, 50 psi O2, 20 h). Since trans-stilbene could be produced not only from benzene but also from phenyl group of PPh3 by migration of its phenyl group to Pd, the competitiveness of benzene and the migratory aptitude of aryl group of triarylphosphine toward styrene has been investigated with various phosphines (PR3: P(p-C6H4CH3)3, P(p-C6H4OCH3)3, P(p-C6H4F)3, P(p-C6H4Cl)3, P(C6H5)3, P(C6H11)3, P(OC4H9n)3, P(CH2C6H5)3 and P(C6F5)3). The yield and selectivity toward trans-stilbene are increased as the basicity of the phosphines increases. The composition of arylated olefin from arylphosphine, in turn, increases as the electronegativity of the substituent on the aryl group of arylphosphines increases.