1991 Fiscal Year Final Research Report Summary
Tandem Carbon Carbon Bond Forming Reaction via Zincate Carbenid
| Project/Area Number |
02650626
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto Institute of Technology |
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Principal Investigator |
HARADA Toshiro Kyoto Institute of Technology, Faculty of Engineering and Design, Associate Professor, 工芸学部, 助教授 (30135628)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Carbenoid / Zincate / Halogen / metal / exchange / Coupling Reaction / Palladium Catalyst |
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| Research Abstract |
The electrophilic character of carbenoids as a-metallated carbocation equivalents has not been fully demonstrated in contrast to their widely studied nucleophilic nature. In the present study, we disclosed that lithium(1bromoalkenyl)(dialkyl)zincate and lithium(1-bromocyclopropyl)(dialkyl)-zincate which can be generated by a Br/Zn exchange reaction of the corresponding gem-dibromo compounds undergo a facile intramolecular alkylation reaction to give alkenyl- and cyclopropylzinc species. Since the resulting organozinc intermediates have potential of undergoing further C-C bond formation, the reaction was extended to the tandem substitution reaction of gem-dibromo compounds via Pd(O)catalyzed arylation, acylation and alkenylation reaction.
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