Carbohydrate-based N-heterocyclic carbene-metal complexes: a new avenue for sustainable catalysts in organic transformations

Krishnaraj, Preethi; Reddy, Sabbasani Rajasekhara

doi:10.1039/d2nj04612a

New J. Chem.

2023

DOI: 10.1039/d2nj04612a

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Carbohydrate-based N-heterocyclic carbene-metal complexes: a new avenue for sustainable catalysts in organic transformations

Preethi Krishnaraj

Sabbasani Rajasekhara Reddy

Abstract: N-heterocyclic carbene (NHC) and their metal complexes have been employed as a catalyst in organic transformations due to its high efficiency, cost-effectiveness, and extraordinary performance. Carbohydrates are inexpensive, nontoxic biomolecules...

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Cited by 3 publications

References 62 publications

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Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Ziems,

Komabayashi,

Lehmann

et al. 2024

Eur J Org Chem

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The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

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Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Ziems,

Komabayashi,

Lehmann

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Investigation of adsorption of Fluorouracil as anticancer drug on C82, Si82, Ti-C82 and Ti-Si82 nanocages

Jihad,

Attawi,

Hussein

et al. 2023

Inorganic Chemistry Communications

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Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

Li,

Peng,

Cao

et al. 2024

Chinese Journal of Organic Chemistry

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2,7-Diaryl substituted fluorenes and fluorenones are widely used in fields of organic semiconductor, chemosensor, and metallocene catalysis. Traditional synthesis methods can not meet the requirements of flexible molecular structures and regulation of diverse properties. Aryl-aryl cross coupling reactions based on the catalysis of Pd and Ni complexes have become efficient methods for the preparation of 2,7-diaryl substituted fluorenes and fluorenones. Various types of metal catalysts with phosphine ligands and N-heterocyclic carbene ligands have been applied. The synthetic methods of 2,7-diaryl substituted fluorenones and 2,7-diaryl substituted fluorenes with or without 9-substitutions, and the conditions for the application of Pd and Ni complexes are reviewed. The challenges of various synthetic methods at present are summarized and a brief outlook on possible solutions is provided. Keywords biaryl; fluorene; fluorenone; luminescent material; metallocene 2,7-二芳基取代芴/芴酮及其衍生物(图 1)具有较好的热稳定性及易于调控结构和性能等优点 [1][2][3] , 不仅成功应用于有机发光 [4][5][6][7] 、晶体管 [8][9][10][11] 和太阳能电池 [12][13] 等有机半导体材料, 还广泛应用于聚集诱导发光 [14][15][16][17] 、化学传感器 [18][19][20][21] 、离子交换和物质传输 [22][23][24][25] 、茂金属聚烯烃催化剂 [26][27] 和网格化学 [28][29] 等众多前沿研究领域, 发展前景广阔.然而, 2,7-二芳基取代芴/芴酮的合成依然面临挑战 (图 2A). 传统合成方法以含有联芳基结构的 2,2'-联苯二甲酸为底物, 在大于 300 ℃的高温下脱水脱羧得到 2,7-二芳基取代芴酮, 再通过还原反应将其转化为 9-无取代 2,7-二芳基取代芴 [30] , 并通过碱性条件下的取代反应进一步生成 9-取代 2,7-二芳基取代芴 [31][32][33] . 该路线不仅产率偏低, 联芳基联苯二甲酸底物的制备是更大的难题.20 世纪 80 年代发展起来的 Kumada、Negishi 和 Suzuki-Miyaura 交叉偶联反应 [34][35][36][37] , 使用 Pd 和 Ni 配合物催化 ArMgX、ArZnX 和 ArB(OR) 2 与卤代芳烃直接高效构建芳基-芳基结构 [38][39] (图 2A), 为 2,7-二芳基取代芴/芴酮的合成提供了行之有效的手段. 以 2,7-二碘芴与苯基格氏试剂在 3 mol%四(三苯基膦)钯(图 2B, M2) 催

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Carbohydrate-based N-heterocyclic carbene-metal complexes: a new avenue for sustainable catalysts in organic transformations

Abstract: N-heterocyclic carbene (NHC) and their metal complexes have been employed as a catalyst in organic transformations due to its high efficiency, cost-effectiveness, and extraordinary performance. Carbohydrates are inexpensive, nontoxic biomolecules...

Cited by 3 publications

References 62 publications

Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Investigation of adsorption of Fluorouracil as anticancer drug on C82, Si82, Ti-C82 and Ti-Si82 nanocages

Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

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Carbohydrate-based N-heterocyclic carbene-metal complexes: a new avenue for sustainable catalysts in organic transformations

Abstract: N-heterocyclic carbene (NHC) and their metal complexes have been employed as a catalyst in organic transformations due to its high efficiency, cost-effectiveness, and extraordinary performance. Carbohydrates are inexpensive, nontoxic biomolecules...

Cited by 3 publications

References 62 publications

Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Investigation of adsorption of Fluorouracil as anticancer drug on C82, Si82, Ti-C82 and Ti-Si82 nanocages

Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

Contact Info

Product

Resources

About

Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction