Copper mediated coupling of 2-(piperazine)-pyrimidine iodides with aryl thiols using Cu(I)thiophene-2-carboxylate

TETRAHEDRON LETTERS

卷:58

Article

Shrestha, Liza¹  Patel, Hardik J.¹  Kang, Yanlong¹  Sharma, Sahil¹  Chiosis, Gabriela^1,2  Taldone, Tony¹ 

[1] Sloan Kettering Inst, Program Chem Biol, New York, NY 10065 USA

[2] Mem Sloan Kettering Canc Ctr, Dept Med, New York, NY 10065 USA

关键词: Diaryl sulfide;    Thioether;    Piperazine;    CuTC;   

DOI  :  10.1016/j.tetlet.2017.10.041

来源: Elsevier

【 摘 要 】

A copper-mediated synthesis of diaryl sulfides utilizing Cu(I)-thiophene-2-carboxylate (CuTC) is described. We demonstrate the use of CuTC as a soluble, non-basic catalyst in the coupling of aryl iodides and aryl thiols in the synthesis of synthetically advanced diaryl sulfides. This method allows for the successful coupling of challenging substrates including ortho-substituted and heteroaryl iodides and thiols. Additionally, most of the aryl iodide substrates used here contain the privileged piperazine scaffold bound to a pyrimidine, pyridine, or phenyl ring and thus this method allows for the elaboration of complex piperazine scaffolds into molecules of biological interest. The method described here enables the incorporation of late-stage structural diversity into diaryl sulfides containing the piperazine ring, thus enhancing the number and nature of derivatives available for SAR investigation. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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