Development of Gold-and Palladium-catalyzed New Transformations via Modification of Ligands

通过配体修饰开发金和钯催化的新转化

• 批准号: 20350015
• 负责人: YAMAMOTO Yoshinori
• 金额: $ 12.31万
• 依托单位: Tohoku University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 2008
• 资助国家: 日本
• 起止时间: 2008 至 2010
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-20350015/
• 关键词: 反応有機化学; 金触媒; パラジウム触媒; リン配位子効果; ヒドロチオル化; 三成分環化反応; 連続的環化反応; D-A-D有機光電材料; 炭素-炭素多結合活性化; カチオン性金触媒; アレン化合物; アルキン化合物; よう素反応剤; 複素環; 不斉ヒドロアミノ化; アルキン; アレン; 不斉配位子

Novel Pd-and Au-catalyzed molecular transformations have been developed through the modification of ligands and counter anions which showed high reactivity and selectivity. A variety of Norbornane derivatives have been synthesized and successfully used in the Pd-catalyzed asymmetric intramolecular hydroamination of alkynes. The newly prepared (R, R)-methyl norphos and (R, R)-toly renorphos afforded N-containing heterocyles in high yields and high enantio-selectivity. Moreover, novel Pd-catalyzed allylative dearomatization and three-component cycloaddition were developed. We have succeeded in development of cationic Au-catalyzed hydroalkoxylation and hydrothiolation. Moreover, we also succeeded in construction of thienocarbazole frameworks via a new Au-catalyzed cascade cyclization of arydiynes, which was further applied in the synthesis of D-A-D organic electronic materials. Various O-, S-and N-containing heterocyles bearing diiodine substituents have been synthesized through the facile and efficient electrophilic iodocyclizations.

通过对配体和抗衡阴离子的修饰，发展了新型的钯和金催化的分子转化反应，表现出高的反应活性和选择性。合成了一系列降冰片烷衍生物，并成功地应用于钯催化的炔的不对称分子内氢胺化反应。新合成的（R，R）-甲基降诺磷和（R，R）-甲苯基降诺磷以高产率和高对映选择性合成了含氮杂环化合物。此外，还发展了新型钯催化烯丙基脱芳构化反应和三组分环加成反应。我们成功地开发了阳离子Au催化的氢烷氧基化和氢硫醇化反应。此外，我们还成功地通过一种新的Au催化芳二炔级联环化反应构建了噻吩并咔唑骨架，并将其进一步应用于D-A-D有机电子材料的合成。通过简便有效的亲电碘环化反应，合成了各种含O、S和N的二碘取代杂环化合物。

项目成果

Gold-catalyzed synthesis of polycyclic enones from carbon tethered 1,3-enynyl carbonyls via tandem heteroenyne metathesis and Nazarov reaction

• DOI: 10.1021/ol801265s
• 发表时间: 2008-07-17
• 期刊: ORGANIC LETTERS
• 影响因子: 5.2
• 作者: Jin, Tienan;Yamamoto, Yoshinori
• 通讯作者: Yamamoto, Yoshinori

π-Electrophilic Lewis Acids Catalyzed New transformations

π-亲电路易斯酸催化新转变

• 发表时间: 2009
• 作者: uchibe;K.; Mayumi;Y.; Wang;K.;Yokota;M.; Ichikawa;J;山本嘉則
• 通讯作者: 山本嘉則

Palladium-catalyzed bisfunctionalization of active alkenes by .-acetonitrile-allyl addition : application to the synthesis of unsymmetric 1, 4-di(organo)fullerene derivatives

钯催化的活性烯烃的.-乙腈-烯丙基加成双官能化：在不对称 1, 4-二（有机）富勒烯衍生物合成中的应用

• 发表时间: 2012
• 期刊: Tetrahedron Lett
• 影响因子: 1.8
• 作者: Lu Shirong;Jin Tienan;Bao Ming;Asiri Abdullah M.;Yamamoto Yoshinori
• 通讯作者: Yamamoto Yoshinori

シグマおよびパイ配位性ルイス酸を用いる分子変換

使用西格玛和皮配位路易斯酸进行分子转化

• 发表时间: 2010
• 作者: T. Yoshikawa;H. Motegi;A. Kakizaki;T. Takayanagi;M. Shiga;M. Tachikawa;Tetsu Kogiso;山本嘉則
• 通讯作者: 山本嘉則

Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight

• DOI: 10.1016/j.tet.2008.11.106
• 发表时间: 2009-02
• 期刊: Tetrahedron
• 影响因子: 2.1
• 作者: Naoko Nishina;Yoshinori Yamamoto