5633-55-6Relevant articles and documents
Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
supporting information, p. 12320 - 12326 (2021/08/09)
Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.
Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids
Gavane, D. S.,Jambhorkar, V. S.,Kale, B. D.,Karnik, K. S.,Khandare, A. L.,Narula, I. S.,Rajhans, A. P.,Sarkate, A. P.
, p. 1300 - 1303 (2020/10/02)
Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.
Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
, p. 4072 - 4085 (2019/04/01)
A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
