Copper mediated coupling of 2-(piperazine)-pyrimidine iodides with aryl thiols using Cu(I)thiophene-2-carboxylate Journal Article
| Authors: | Shrestha, L.; Patel, H. J.; Kang, Y.; Sharma, S.; Chiosis, G.; Taldone, T. |
| Article Title: | Copper mediated coupling of 2-(piperazine)-pyrimidine iodides with aryl thiols using Cu(I)thiophene-2-carboxylate |
| Abstract: | 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. © 2017 Elsevier Ltd |
| Keywords: | unclassified drug; structure activity relation; substitution reaction; chemical structure; pyrimidine derivative; catalyst; copper; synthesis; pyrimidine; sulfide; thiophene derivative; chemical reaction kinetics; thiol derivative; iodine derivative; piperazine; article; cutc; diaryl sulfide; thioether; 2 (piperazine) pyrimidine iodide; aryl iodide; aryl thiol derivative; copper thiophene 2 carboxylate; pyridine |
| Journal Title: | Tetrahedron Letters |
| Volume: | 58 |
| Issue: | 48 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2017-11-29 |
| Start Page: | 4525 |
| End Page: | 4531 |
| Language: | English |
| DOI: | 10.1016/j.tetlet.2017.10.041 |
| PROVIDER: | scopus |
| PMCID: | PMC6047360 |
| PUBMED: | 30026636 |
| DOI/URL: | |
| Notes: | Article -- Export Date: 4 December 2017 -- Source: Scopus |
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