通过轻微而高效的Pd催化形成与酸的B-C键,使多德卡酸的功能化
Mahmoud K Al-Joumhawy1, Jui-Chi Chang1, Khaleel I Assaf2
1School of Science, Constructor University, Campus Ring 1, 28759, Bremen, Germany.
Chemistry (Weinheim an der Bergstrasse, Germany)
|October 4, 2023
概括
研究人员开发了一种新的方法,通过B-C键将无机二二甲酸盐与有机分子联系起来. 这种木-米亚乌拉合方法可以创建用于各种应用的新型混合有机-无机材料.
科学领域:
- 化学 化学 化学
- 材料科学 材料科学 材料科学
- 有机化学 有机化学
背景情况:
- 混合有机-无机分子为生物和材料科学应用提供独特的特性.
- 直接将无机集群与有机构建块联系起来是一项挑战.
- 集群,如十二甲酸盐,对新型材料的开发有兴趣.
研究的目的:
- 建立一种新的合成策略,直接将十二甲酸盐集群与有机部分联系起来.
- 探索木-米亚乌拉合在无机团和有机分子之间形成BC键的实用性.
- 为了证明新方法的功能组耐受性和基质范围.
主要方法:
- 使用酸作为有机构建块上的功能组.
- 使用的苏苏基-米亚乌拉合条件与-无二二二甲.
- 优化的配体 (DavePhos) 和溶剂 (N-methylpyrrolidone,CD3CN) 是成功合的选择.
- 研究了与各种有机基质的反应,包括电子贫基.
主要成果:
- 成功地在十二甲酸盐集群和有机构建块之间建立了直接的B-C键连接.
- 在这种特定的无机-有机链路上证明了木-米亚乌拉合的有效性.
- 确定了特定配体和溶剂在实现高产量的关键作用.
- 证实了该方法的功能组耐受性和适用于广泛的基板的适用性.
结论:
- 开发了一种新的,多功能合成方法,用于创建具有直接二甲基酸碳链接的混合有机-无机分子.
- 木-米亚乌拉合提供了一个高效的路线,以有机成分功能化无机集群.
- 这种方法为设计具有定制性质的先进材料和功能分子打开了道路.
相关概念视频
Hydroboration-Oxidation of Alkenes
8.3K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
8.3K
Regioselectivity and Stereochemistry of Hydroboration
8.2K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.2K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
18.2K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.2K
Cationic Chain-Growth Polymerization: Mechanism
2.3K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
2.5K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.5K


