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1991 Fiscal Year Final Research Report Summary

Mechanism of Aryldestannylation of Alkenylstannanes with Arylpalladium Complexes

Research Project

Project/Area Number 02640413
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKinki University

Principal Investigator

KIKUKAWA Kiyoshi  Kinki University in Kyushu, Faculty of Engineering, Department of Industrial Chemistry, Professor, 工学部・工業化学科, 教授 (60037918)

Project Period (FY) 1990 – 1991
KeywordsAlkenylstannanes / Organotins / Organopalladium / Homogeneous Catalyst / Transmetallation / C-C Coupling / Arylation / Electrophilic Substitution
Research Abstract

Both ArPd(PPh_3)_2I and ArPd(PPh_3)_2BF_4 aryldestannylated PhCH=CHSnR_3 and Ph(R_3Sn)C=CH_2(R=Bu, Ph)to give PhCH=CHAr and Ph(Ar)C=CH_2, respectively. In the absence of strong neutral ligands such as PPh@_3, however, the counter anion of the palladum complexes showed drastic effect on the reaction profile. Reaction with PhCH=CHSnR_3, [ArPd]^+BF_4^- gave Ph(Ar)C=CH_2, whereas Ar-Pd-I gave PhCH=CHAr.
In the presence of coordinatively strong ligands such as PPh_3 or I^-, arylpalladium complexes aryldestannylate alkenylstannanes via transmetallation-reductive elimination mechanism as following scheme.
<<chemical formula>>
In the absence of coordinatively strong ligands, the reaction with [Ar-Pd]^+BF_4^- proceeds through addition-elimination mechanism as following scheme.
<<chemical formula>>
In the palladium catalyzed C-C coupling of organic electrophiles with organometallics, organs-palladium species expect to be a key intermediate. Present results exemplify an important role of the ligands of organopalladium intermediates to design reaction pathway.

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Published: 1993-03-16  

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