Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation

Mukherjee, A. K.; Basu, Srinka; Bhattacharya, Samaresh

doi:10.1016/j.ica.2019.119228

Cited by 5 publications

(2 citation statements)

References 74 publications

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“…The diimine moiety in the 1,4‐diazabutadiene ligands is known to undergo two one‐electron reductions with a gap of about 500 mV. [ 18 ] Hence the first (–0.56 to –0.70 V) and the third (–1.21 to –1.39 V) reductive responses are tentatively assigned to reductions of the diimine fragment. The second reduction (–0.74 to –0.89 V) is assigned, by comparing with cyclic voltammetric properties of reported ruthenium(II)‐trpy complexes, to reduction of trpy.…”

Section: Resultsmentioning

confidence: 99%

Heteroleptic 1,4‐Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation

2020

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Reaction of [Ru(trpy)Cl3] with 1,4‐diazabutadienes (p‐RC6H4N=C(H)‐(H)C=NC6H4R‐p; R = OCH3, CH3, H and Cl; abbreviated as L‐R) in refluxing ethanol in the presence of triethylamine has afforded a family of complexes, isolated as perchlorate salts, of type [Ru(trpy)(L‐R)Cl]ClO4 [depicted as complexes 1 (R = OCH3), 2 (R = CH3), 3 (R = H) and 4 (R = Cl)]. Crystal structures of complexes 1, 2 and 4 have been determined, and structure of complex 3 has been optimized by DFT method. The 1,4‐diazabutadiene ligand in each complex is bound to ruthenium as a N,N‐donor forming five‐membered chelate. Complexes 1–4 catalyze transfer hydrogenation of aryl aldehydes to the corresponding alcohols with high (ca. 106) TON. They are also found to catalyze transfer hydrogenation of aryl ketones to corresponding secondary alcohols, but with much less efficiency. Catalytic transfer hydrogenation of nitroarenes to the corresponding amines has also been achieved.

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Section: Resultsmentioning

confidence: 99%

Heteroleptic 1,4‐Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation

2020

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“…2020 年, Bhattacharya 课题组 [22] 发展了一类含芳香环的 2020 年, Emerson 等 [23] 详细探究了 1,10-邻菲啰啉 (phen)配体对铜配合物的电子结构和氧化还原性的影响 6)} (Scheme 5). X 单晶衍射分析表明, 这些配体微妙地影响着铜离子的配位构型.…”

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Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes

Jia¹,

Tong²

2022

Chinese Journal of Organic Chemistry

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Copper-catalyzed Chan-Lam reaction represents an important and highly efficient method for the synthesis of organic molecules containing carbon-heteroatom (C-N, C-O, C-S) bonds, which has many advantages such as mild conditions, wide substrates range and high yields. Therefore, the Chan-Lam coupling reactions are extensively applied in organic synthesis, medicinal chemistry and material science, etc. Although many catalytic systems using different copper salt alone or in combination with various ligands for Chan-Lam coupling reaction have been extensively reported by different groups, the studies on the Chan-Lam coupling reaction employing well-defined copper complexes as catalysts were underdeveloped. In recent years, the Chan-Lam reactions catalyzed by copper complexes with different ligands have attracted more special attention from synthetic chemist and made many achievements. Some novel copper complexes have been designed and synthesized, which were further used as efficient catalysts for Chan-Lam coupling reactions of arylboronic acids with various nucleophiles. The recent progresses on Chan-Lam coupling reactions catalyzed by well-defined copper(II) complexes are summarized from two aspects of homogeneous catalysis and heterogeneous catalysis in detail. Then the homogeneous Chan-Lam reactions are classified by the different coordination mode of copper complexes, and the heterogeneous Chan-Lam reactions are described according to chronological order. The reaction mechanism on Chan-Lam coupling proposed by different research groups is also straightened out and discussed. Finally, the development prospects of this research field are pointed out. Keywords copper(II) complex; arylboronic acid; nucleophile; Chan-Lam coupling; N-arylation Chan-Lam 偶联反应, 也叫 Chan-Evans-Lam 偶联, 是指铜盐催化(或促进)下芳基硼酸(或锡烷、硅氧烷)与含 N-H、 O-H 或 S-H 的化合物进行氧化偶联形成芳基碳-杂原子键的反应(Scheme 1). 该反应是在 1998 年由 Chan [1] 、Evans [2] 和 Lam [3] 等同时发现并独立报道的. 相比钯催化 N-芳基化或 O-芳基化的 Buchwald-Hartwig 偶联反应, Chan-Lam 反应使用廉价易得的铜盐作为催化剂, 在室温和敞开体系中进行, 具有条件温和、底物

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Development of phosphine and diimine stabilized copper(I) catalysts for efficient azide–alkyne cycloaddition

Pradhan,

Mukherjee,

Bhattacharya

2025

Inorganica Chimica Acta

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Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation

Cited by 5 publications

References 74 publications

Heteroleptic 1,4‐Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation

Heteroleptic 1,4‐Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation

Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes

Development of phosphine and diimine stabilized copper(I) catalysts for efficient azide–alkyne cycloaddition

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