Copper cluster complex-catalyzed C-S bond formation

被引：0

作者：

Liao, Nien-Chi Chang ^{[1
]}

Basha, R. Sidick ^{[1
]}

Shih, Bo-Hao ^{[1
]}

Liu, Chia-Chun ^{[1
]}

Wang, Miao-Han ^{[1
]}

Lin, Po-Heng ^{[1
]}

Lee, Chin-Fa ^{[1
,2
,3
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

[2] Natl Chung Hsing Univ, iCtr Adv Sci & Technol iCAST, Taichung 402, Taiwan

[3] Natl Chung Hsing Univ, Innovat & Dev Ctr Sustainable Agr IDCSA, Taichung 402, Taiwan

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2024年 / 14卷 / 22期

关键词：

METAL-FREE; THIOLS; SULFUR; THIOESTERS; ALDEHYDES;

D O I：

10.1039/d4cy00968a

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Three distinct copper cluster complexes (A-C) containing Cu-O ligated Schiff-base ligands were synthesized and their bonding was investigated by single-crystal X-ray crystallographic studies. These complexes effectively catalyze the C-S cross coupling reaction of less reactive aliphatic thiols to synthesize thioether derivatives. This coupling reaction also tolerates well and is compatible with aryl thiols. The peculiar C(sp2)-SC(sp3) bond formation distinctly took place with high efficiency using low loading of copper cluster complex catalysts. The present report describes an alternative protocol to construct active copper cluster complexes from readily accessible, cheap and efficient ligands. These complexes are air stable, practical, easy to handle and catalyze C-S coupling reactions with good yields. Three distinct copper cluster complexes (A-C) were synthesized and their bonding was investigated by XRD studies. These complexes effectively catalyze the C-S coupling reaction of less reactive aliphatic thiols to synthesize thioether derivatives.

引用

页码：6609 / 6620

页数：12

共 43 条

[1] Carbon-Sulfur Bond Constructions: From Transition-Metal Catalysis to Sustainable Catalysis [J].

Annamalai, Pratheepkumar ;

Liu, Ke-Chien ;

Singh Badsara, Satpal ;

Lee, Chin-Fa .

CHEMICAL RECORD, 2021, 21 (12) :3674-3688

[2] Metal-free sp3 C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes [J].

Badsara, Satpal Singh ;

Liu, Yi-Chen ;

Hsieh, Ping-An ;

Zeng, Jing-Wen ;

Lu, Shao-Yi ;

Liu, Yi-Wei ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2014, 50 (77) :11374-11377

[3] Oxidation of methane by a biological dicopper centre [J].

Balasubramanian, Ramakrishnan ;

Smith, Stephen M. ;

Rawat, Swati ;

Yatsunyk, Liliya A. ;

Stemmler, Timothy L. ;

Rosenzweig, Amy C. .

NATURE, 2010, 465 (7294) :115-U131

[4] Iodine-Mediated Direct Generation of o-Quinone Methides at Room Temperature: A Facile Protocol for the Synthesis of ortho-Hydroxybenzyl Thioethers [J].

Basha, R. Sidick ;

Chen, Chia-Wei ;

Reddy, Daggula Mallikarjuna ;

Lee, Chin-Fa .

CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) :2475-2483

[5] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2022, 122 (21) :16110-16293

[6]

Block E., 1978, REACTIONS ORGANOSULF

[7] Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp Isolate from a Hawaiian Soil Sample [J].

Cai, Shengxin ;

King, Jarrod B. ;

Du, Lin ;

Powell, Douglas R. ;

Cichewicz, Robert H. .

JOURNAL OF NATURAL PRODUCTS, 2014, 77 (10) :2280-2287

[8] Controlled oxidation of hydrocarbons by the membrane-bound methane monooxygenase: The case for a tricopper cluster [J].

Chan, Sunney I. ;

Yu, Steve S. -F. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :969-979

[9]

Chavan S. A., 2001, CHEM COMMUN, V1124

[10] CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chloridess [J].

Chen, Chia-Wei ;

Chen, Yi-Ling ;

Reddy, Daggula Mallikarjuna ;

Du, Kai ;

Li, Chao-En ;

Shih, Bo-Hao ;

Xue, Yung-Jing ;

Lee, Chin-Fa .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (42) :10087-10091

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