A New Medium for Catalyzed C-C Bond Formation Reactions
催化 C-C 键形成反应的新介质
基本信息
- 批准号:14078201
- 负责人:
- 金额:$ 15.36万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research on Priority Areas
- 财政年份:2002
- 资助国家:日本
- 起止时间:2002 至 2005
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
1. Catalytic C-H BorylationDirect C-H borylation of arenes catalyzed by a transition metal complex was studied as an economical protocol for the synthesis of a variety of arylboron compounds. Ir/bipyridine-catalyzed C-H borylation of arenes, heteroarenes, and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane furnished aryl-, heteroaryl-, and benzylboron compounds.2. Carbon-Carbon Bond Formation via the Rhodium Catalyzed Addition Reactions in aqueous mediumVarious rhodium(I) complexes catalyzed the 1,4-addition of organoboronic acids to a,β-unsaturated carbonyl compounds or the Grignard-type addition to aldehydes in a mixture of an organic solvent and water. The reaction provided a convenient method for the asymmetric carbon-carbon bond formation. The rhodium-catalyzed conjugate addition of arylboronic acids to a,β-unsaturated ketones, esters or amides was carried out in water. A complex between [RhCl(cod)]_2 and 2β -cyclodextrin-[Rh(OH)(cod)]_2 catalyzed the … More reaction efficiently in a single aqueous medium.3. Chiral Bis-phosphoramidites for Asymmetric Rhodium-Catalyzed 1,4-AdditionsA chiral bidentate phosphoramidite (BIPAM) was synthesized from Shibasaki's linked-(R)-BINOL and P(NMe_2)_3 as a new ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to a,β-unsaturated carbonyl compounds. The effects of BIPAM and Feringa's monodentate phosphoramidite on the yields and enantioselectivities were investigated. The reaction was significantly accelerated in the presence of a base such as KOH and Et3N, allowing the reaction to be completed at the lower temperatures than 50℃.4. Palladium-Catalyzed Addition Reactions of Organoboron compounds.An enantioselective synthesis of cyclic and acyclic β-aryl ketones and esters via palladium(II)-catalyzed 1,4-addition of Ar-[m] (m=B(OH)_2, BF_3K, Si(OMe)_3, SiF_3, BiAr_2) to α, β-unsaturated ketones or esters is discovered. The enantioselection mechanism and efficiency of a chiraphos ligand for structurally planar α, β-unsaturated ketones are discussed on the basis of the X-ray structure of the catalyst and results of DFT computational studies on the modes of coordination of the substrates to the phenylrhodium(I)/(S,S)-chiraphos intermediate. Less
1.催化C-H硼化反应研究了过渡金属配合物催化的芳烃直接C-H硼化反应,作为合成各种芳基硼化合物的经济方案,通过双联芳烃、杂芳烃和烷基芳烃的苄基位置进行Ir/联吡啶催化的C-H硼化反应。 (频那醇)二硼或频哪醇硼烷配备的芳基-,杂芳基和苄基硼化合物。2.通过铑催化加成反应在水介质中形成碳-碳键各种铑(I)络合物催化有机硼酸与a,β-不饱和羰基化合物或格氏加成反应该反应为不对称碳-碳键的形成提供了一种简便的方法。 [RhCl(cod)]_2 和 2β-环糊精-[Rh(OH)(cod) 之间在铑催化下,将芳基硼酸与 α,β-不饱和酮、酯或酰胺进行共轭加成。 )]_2 在单一水介质中有效催化…更多反应。 3. 手性双亚磷酰胺铑催化的1,4-加成以Shibasaki的连接-(R)-BINOL和P(NMe_2)_3合成手性二齿亚磷酰胺(BIPAM)作为铑(I)催化芳基硼酸不对称1,4-加成的新配体BIPAM 和 Feringa 单齿化合物的作用。研究了亚磷酰胺对收率和对映选择性的影响,在KOH和Et3N等碱存在下,反应明显加速,使得反应在低于50℃的温度下完成。4. .通过钯(II)催化对映选择性合成环状和无环β-芳基酮和酯发现了Ar-[m] (m=B(OH)_2, BF_3K, Si(OMe)_3, SiF_3, BiAr_2)与α,β-不饱和酮或酯的1,4-加成反应的对映选择机制和效率。基于催化剂的 X 射线结构和配位模式的 DFT 计算研究结果,讨论了结构平面 α, β-不饱和酮的 chiraphos 配体苯基铑(I)/(S,S)-chiraphos中间体的底物较少。
项目成果
期刊论文数量(241)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Asymmetric 1,4-addition of triarylbismuths to enones catalyzed by dicationic palladium(II) complexes.
- DOI:10.1039/b407272c
- 发表时间:2004-08
- 期刊:
- 影响因子:4.9
- 作者:T. Nishikata;Yasunori Yamamoto;N. Miyaura
- 通讯作者:T. Nishikata;Yasunori Yamamoto;N. Miyaura
T.Ishiyama: "Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group : efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility."Journal of Organomet
T.Ishiyama:“钯催化双(频哪醇)二硼与被羰基β-取代的乙烯基三氟甲磺酸酯的交叉偶联反应:β-硼基-α,β-不饱和羰基化合物的有效合成及其合成实用性。”杂志有机气象学报
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
Metal-catalyzed reaction of diborons for synthesis of organoboron compounds.
用于合成有机硼化合物的二硼金属催化反应。
- DOI:
- 发表时间:2004
- 期刊:
- 影响因子:0
- 作者:T.Ishiyama;N.Miyaura
- 通讯作者:N.Miyaura
Preparation of electron-withdrawing group-containing compounds using palladium complex catalysts.
使用钯络合物催化剂制备含吸电子基团的化合物。
- DOI:
- 发表时间:2004
- 期刊:
- 影响因子:0
- 作者:Miyaura;N.
- 通讯作者:N.
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