Boron-Masking Strategy for New Transformations of Organoboronic Acids

有机硼酸新转化的硼掩蔽策略

• 批准号: 19205007
• 负责人: SUGINOME Michinori
• 金额: $ 32.53万
• 依托单位: Kyoto University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (A)
• 财政年份: 2007
• 资助国家: 日本
• 起止时间: 2007 至 2010
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-19205007/
• 关键词: 合成有機化学; 有機ボロン酸; クロスカップリング; 反復合成; 保護基; マスキング; アントラニルアミド; オルト位C-H結合活性化; 配向基; 有機合成化学; 1,8-ジアミノナフタレン; ジボリル化; 脱水素ホウ素化; 分枝オリゴアレーン; C-H官能基化; クロスカップリソグ; 繰り返し合成; デンドリマー; オリゴ(フェニレン-ビニレン)

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.

通过凝结将“掩盖组”引入有机碳酸硼原子的基础上，已经开发出了高度功能化有机酸合成的新方法。 1，8-二氨氧甲甲乙烯是一个高度强大的保护组，尤其是在铃木中。 Miyaura耦合。掩蔽组允许通过迭代交叉偶联，寡素（苯基 - 乙烯基）S的迭代合成以及基于寡头的树枝状的简便合成。 Diboron试剂，其中有两个硼原子之一被保护并用于炔烃枯萎反应中，从而导致二抗产物的区域选择性形成，这适用于逐步的交叉偶联反应。 2-（吡唑-5-基）苯胺（PZA）和苯烷酰胺（AAM）的冷凝物与有机酸盐酸经过氟苯甲硅烷二硅化二硅化，其中含氮的膜掩蔽组（PZA和AAM）作为Ortho indriendiendectectional indirective ottriendionallation-syminallation。 ，反应后很容易移动。 AAM集团还曾担任铃木的Boronyl集团的保护组。 Miyaura耦合。

项目成果

Protection of Boronyl Groups for the Synthesis of Functionalized Organoboronic Acid Derivatives

硼基基团的保护用于合成功能化有机硼酸衍生物

• 发表时间: 2009
• 作者: Suginome;M.
• 通讯作者: M.

High-Molecular-Weight Polyquinoxaline-Phosphine (PQXphos) as an Efficient Chiral Ligand for Asymmetric Biaryl Synthesis by Suzuki-Miyaura Coupling

高分子量聚喹喔啉-膦 (PQXphos) 作为一种高效手性配体，用于铃木-宫浦偶联合成不对称联芳基

• 发表时间: 2011
• 期刊: Angew.Chem., Int.Ed.
• 作者: Mori;T.;他;Michinori Suginome
• 通讯作者: Michinori Suginome

Boron-masking strategy for selective synthesis of oligoarylboronic acids via cross-coupling reactions

通过交叉偶联反应选择性合成低聚芳基硼酸的硼掩蔽策略

• 发表时间: 2008
• 作者: Suginome;M.
• 通讯作者: M.

Nickel-Catalyzed Addition of Alkyne C-H Bonds to 1, 3-Dienes and Styrenes

镍催化炔烃 C-H 键加成至 1, 3-二烯和苯乙烯

• 发表时间: 2008
• 作者: 半沢公也;石川尚子;田邉真;小坂田耕太郎;藤井朱鳥;山本正伸;Michinori Suginome
• 通讯作者: Michinori Suginome

New Metal-Mediated Organic Synthesis by Virtue of New Protecting, Directing, and Reacting Groups on the Boron Atoms of Organoboronic Acids

利用有机硼酸硼原子上的新保护、导向和反应基团进行新金属介导的有机合成

• 发表时间: 2010
• 作者: Suginome;M.
• 通讯作者: M.