2010 Fiscal Year Final Research Report
Boron-Masking Strategy for New Transformations of Organoboronic Acids
| Project/Area Number |
19205007
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
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| Project Period (FY) |
2007 – 2010
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| Keywords | 合成有機化学 |
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| Research Abstract |
New methods for the synthesis of highly functionalized organoboronic acids have been developed on the basis of introduction of "masking groups" onto the boron atoms of organoboronic acids by condensation. 1, 8-Diaminonaphthalene served as a highly robust protecting group particularly in Suzuki. Miyaura coupling. The masking group allowed synthesis of oligoarenes via iterative cross-coupling, iterative synthesis of oligo(phenylene-vinylene) s, and facile synthesis of oligoarene-based dendrons. A diboron reagent in which one of the two boron atoms is protected has been prepared and used in the alkyne diboration reaction, leading to regioselective formation of diboration products, which were applicable to stepwise cross-coupling reactions. Condensates of 2-(pirazol-5-yl) aniline(PZA) and anthranilamide(AAM) with organoboronic acids underwent ruthenium-catalyzed ortho-silylation, in which the nitrogen-containing masking groups(PZA and AAM) served as ortho-directing groups, which are easily removable after the reaction. The AAM group also served as a protecting group for the boronyl group in the Suzuki. Miyaura coupling.
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