Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction

Zhou, Zhonggao; Xie, Qian; Li, Jing; Yuan, Yangyang; Liu, Yong; Liu, Yulong; Lu, Dongliang; Xie, Yong‐Rong

doi:10.1007/s10562-021-03654-0

Cited by 11 publications

(10 citation statements)

References 70 publications

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“…10 [54] 11 [50] 12 [50] Ar Ar 13 [26,40,41] Ar = 14 [26] 15 [26] 16 [26] 17 [26,42] 18 [26,43,60,64] 19 [27,43,61,64] 20 [27] OMe Ar Ar 37 [56] Ar = 38 [56] 41 [56] 42 [56] 43 [56] 44 [56] F F F OMe CN S S 39 [56] 40 [56] 21 [57] CHO 22 [11] Ph 26 [58] F CF 3…”

Section: O Ar Armentioning

confidence: 99%

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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Section: O Ar Armentioning

confidence: 99%

Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

Li,

Peng,

Cao

et al. 2024

Chinese Journal of Organic Chemistry

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“…Recently, Zhou et al have reported the first pure b-anomerbased Pd-CNHC complexes in a two-step process starting from commercially available glucose materials, as shown in Scheme 9. 46 In addition, the small alkyl groups 21a-c tagged on NHC produces distinct a and b isomers, whereas the highly steric 2,5-dimethylphenyl group present on the N atom of NHC restricts the rotation of anomeric carbon to produce pure The developed protocol uses a green solvent mixture of EtOH/H 2 O and follows the concept of green chemistry and the products are significant for the synthesis of conjugated organic small molecular materials, as represented in Scheme 10.…”

Section: Synthesis Of Cnhc-palladium Metal Complexesmentioning

confidence: 99%

“…Recently, Zhou et al have reported the first pure β-anomer-based Pd–CNHC complexes in a two-step process starting from commercially available glucose materials, as shown in Scheme 9. 46…”

Section: Carbohydrate-based Nhc-metal Complexesmentioning

confidence: 99%

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

Krishnaraj

Reddy

2023

New J. Chem.

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“…Among the few examples of PEPPSI-Pd complexes containing NHC ligands with potential additional sigma donor moieties, we can include the 2-hydroxyethyl-substituted complexes reported by Aktas and co-workers, which efficiently catalyze the Suzuki–Miyaura coupling of a variety of aryl chlorides with boronic acids using water as the solvent . Özdemir et al and Zhou et al prepared independently a series of PEPPSI derivatives bearing 3-methyl oxetane and glucopyranosides, respectively, and demonstrated their application in Heck and Sonogashira cross-couplings. It is worth mentioning that in these three examples, no coordination of the extra donor moiety was reported.…”

Section: Introductionmentioning

confidence: 99%

“…10 O ̈zdemir et al and Zhou et al prepared independently a series of PEPPSI derivatives bearing 3-methyl oxetane 11 and glucopyranosides,12 respectively, and demonstrated their application in Heck and Sonogashira cross-couplings. It is worth mentioning that in these three examples, no coordination of the extra donor moiety was reported.…”

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confidence: 99%

Mercaptopyridine-Functionalized MIC-Pd(II)-PEPPSI Complexes: Synthesis and Hemilability Effect in Catalytic Applications

Patricio-Rangel,

González-Silva,

Mendoza-Espinosa

2023

Organometallics

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Palladium(II)-PEPPSI-type complexes bearing 2- or 4-mercaptopyridine-functionalized 1,2,3-triazolylidenes (4 and 5, respectively) have been prepared and fully characterized. Complexes 4 and 5 show high catalytic activity in the Suzuki–Miyaura coupling of aryl chlorides with ortho-substituted boronic acids under mild reaction conditions. The effect of the mercaptopyridine substituent in the preparation of cyclometalated derivatives was investigated by the treatment of 4 and 5 with an excess of AgSbF6. The dehalogenation process allows the preparation of the dicationic complex 7, in which the nitrogen atom of the 2-mercaptopyridine coordinates the palladium center, forming a seven-membered ring. The isolation of the respective derivative with the 4-mercaptopyridine was unsuccessful. Complex 7 efficiently catalyzes the intermolecular hydroamination between anilines and terminal alkynes without the need for additives and shows good group tolerance. A key feature for the successful catalytic hydroamination relies on the hemilability of the 2-mercaptopyridine wingtip confined to the proximity of the alkynophilic metal active site, which favors a series of proton transfers, the process which is not possible when complexes 4 or 5 are employed as catalysts.

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Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction

Cited by 11 publications

References 70 publications

Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones

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

Mercaptopyridine-Functionalized MIC-Pd(II)-PEPPSI Complexes: Synthesis and Hemilability Effect in Catalytic Applications

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