Development of new catalytic C-C bond-forming reactions other than allylation reactions via alpha-silyl-substituted sigma-allylpalladium intermediates
Project/Area Number |
24550115
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Synthetic chemistry
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Research Institution | University of Toyama |
Principal Investigator |
HORINO Yoshikazu 富山大学, 大学院理工学研究部(工学), 准教授 (30447651)
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Project Period (FY) |
2012-04-01 – 2015-03-31
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Project Status |
Completed (Fiscal Year 2014)
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Budget Amount *help |
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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Keywords | パラジウム / メタロイド / アリル化 / シクロプロパン化 / 二量化 / 三成分連結反応 / アリルパラジウム / アリルボロネート / カップリング反応 / ホモアリルアルコール / パラジウムカルベノイド / パラダシクロブテン / 二量化反応 / アルケニルホウ素 / アリルホウ素 / シクロプロパン化反応 |
Outline of Final Research Achievements |
We have developed new methods for the generation of putative palladacyclobutene intermediates and palladium carbenoid intermediates from α-metalloid-substituted σ-allylpalladium intermediates. These intermediates then undergo stereoselective cyclopropanation of strained alkenes and self-dimerization of palladium carbenoid intermediates, respectively. Furthermore, the three-component reaction proceeded to provide (Z)-anti-homoallylic alcohols with high diastereoselectivities and high level of alkene stereocontrols if the metalloid-substituted allylacetates, aldehydes, and organoboranes are treated in the presence of palladium catalyst. The present reaction is believed to proceed via an allylation of aldehydes followed by coupling reaction of vinylpalladium intermediates with organoboranes. Thus, we have demonstrated that α-metalloid-substituted π-allylpalladium intermediates can be used for carbon-carbon bond forming-reaction other than allylation reactions.
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Report
(4 results)
Research Products
(26 results)
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[Journal Article] Practical and Convenient Synthesis of 1,6-Di- or 1,2,5,6-Tetraarylhexa-1,3,5-trienes by the Dimerization of Pd(0)-Complexed Alkenylcarbenes Generated from π-Allylpalladium Intermediates2014
Author(s)
Yoshikazu Horino, Yu Takahshi, Kaori Koketsu, Hitoshi Abe, Kiyoshi Tsuge
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Journal Title
Organic Letters
Volume: 16
Issue: 12
Pages: 3184-3187
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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