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Copper in Cross-Coupling Reactions: II. Arylation of Thiols

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Abstract

The review presents an analysis of the recent literature on the use of copper catalysis in the formation of a C-S bond between aryl halides and thiols. The review covers the use of ligand-free systems, water as a solvent, and recyclable catalysts.

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References

  1. Minghao, F., Bingqing, T., Steven, H.L., and Xuefeng, J., Curr. Top. Med. Chem., 2016, vol. 16, p. 1200. https://doi.org/10.2174/1568026615666150915111741

    Article  CAS  Google Scholar 

  2. Ghaderi, A., Tetrahedron, 2016, vol. 72, p. 4758. https://doi.org/10.1016/j.tet.2016.06.067

    Article  CAS  Google Scholar 

  3. Lee, C.-F., Liu, Y.-C., and Badsara, S.S., Chem. Asian J., 2014, vol. 9, p. 706. https://doi.org/10.1002/asia.201301500

    Article  CAS  PubMed  Google Scholar 

  4. Kumar, S. and Engman, L., J. Org. Chem., 2006, vol. 71, p. 5400. https://doi.org/10.1021/jo060690a

    Article  CAS  PubMed  Google Scholar 

  5. Taniguchi, N. and Onami, T., J. Org. Chem., 2004, vol. 69, p. 915. https://doi.org/10.1021/jo030300+

    Article  CAS  PubMed  Google Scholar 

  6. Taniguchi, N., J. Org. Chem., 2004, vol. 69, p. 6904. https://doi.org/10.1021/jo040184q

    Article  CAS  PubMed  Google Scholar 

  7. Wang, H., Jiang, L., Chen, T., and Li, Y., Eur. J. Org. Chem., 2010, vol. 2010, p. 2324. https://doi.org/10.1002/ejoc.201000003

    Article  CAS  Google Scholar 

  8. Martinek, M., Korf, M., and Srogl, J., Chem. Commun., 2010, vol. 46, p. 4387. https://doi.org/10.1039/c002725a

    Article  CAS  Google Scholar 

  9. Lumb, I., Hundal, M.S., and Hundal, G., Inorg. Chem., 2014, vol. 53, p. 7770. https://doi.org/10.1021/ic501141m

    Article  CAS  PubMed  Google Scholar 

  10. Yamamoto, T. and Sekine, Y., Can. J. Chem., 1984, vol. 62, p. 1544. https://doi.org/10.1139/v84-263

    Article  CAS  Google Scholar 

  11. Schopfer, U. and Schlapbach, A., Tetrahedron, 2001, vol. 57, p. 3069. https://doi.org/10.1016/S0040-4020(01)00157-0

    Article  CAS  Google Scholar 

  12. Fernández-Rodríguez, M.A., Shen, Q., and Hartwig, J.F., J. Am. Chem. Soc., 2006, vol. 128, p. 2180. https://doi.org/10.1021/ja0580340

    Article  PubMed  CAS  Google Scholar 

  13. Barbiéri, R.S., Bellato, C.R., Dias, A.K.C., and Massabni, A.C., Catal. Lett., 2006, vol. 109, p. 171. https://doi.org/10.1007/s10562-006-0074-2

    Article  CAS  Google Scholar 

  14. Fernández-Rodríguez, M.A. and Hartwig, J.F., J. Org. Chem., 2009, vol. 74, p. 1663. https://doi.org/10.1021/jo802594d

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  15. Byeun, A., Baek, K., Han, M.S., and Lee, S., Tetrahedron Lett., 2013, vol. 54, p. 6712. https://doi.org/10.1016/j.tetlet.2013.09.074

    Article  CAS  Google Scholar 

  16. Zhang, Y., Ngeow, K.C., and Ying, J.Y., Org. Lett., 2007, vol. 9, p. 3495. https://doi.org/10.1021/ol071248x

    Article  CAS  PubMed  Google Scholar 

  17. Jammi, S., Barua, P., Rout, L., Saha, P., and Punniyamurthy, T., Tetrahedron Lett., 2008, vol. 49, p. 1484. https://doi.org/10.1016/j.tetlet.2007.12.118

    Article  CAS  Google Scholar 

  18. Zhang, J., Medley, C.M., Krause, J.A., and Guan, H., Organometallics, 2010, vol. 29, p. 6393. https://doi.org/10.1021/om100816d

    Article  CAS  Google Scholar 

  19. Guan, P., Cao, C., Liu, Y., Li, Y., He, P., Chen, Q., Liu, G., and Shi, Y., Tetrahedron Lett., 2012, vol. 53, p. 5987. https://doi.org/10.1016/j.tetlet.2012.08.055

    Article  CAS  Google Scholar 

  20. Correa, A., Carril, M., and Bolm, C., Angew. Chem. Int. Ed., 2008, vol. 47, p. 2880. https://doi.org/10.1002/anie.200705668

    Article  CAS  Google Scholar 

  21. Wu, W.-Y., Wang, J.-C., and Tsai, F.-Y., Green Chem., 2009, vol. 11, p. 326. https://doi.org/10.1039/b820790a

    Article  CAS  Google Scholar 

  22. Wu, J.-R., Lin, C.-H., and Lee, C.-F., Chem. Commun., 2009, vol. p. 4450. https://doi.org/10.1039/b907362k

    Google Scholar 

  23. Sindhu, K.S., Thankachan, A.P., Thomas, A.M., and Anilkumar, G., Tetrahedron Lett., 2015, vol. 56, p. 4923. https://doi.org/10.1016/j.tetlet.2015.06.087

    Article  CAS  Google Scholar 

  24. Akkilagunta, V.K., Reddy, V.P., and Rao, K.R., Synlett, 2010, vol. 2010, p. 1260. https://doi.org/10.1055/s-0029-1219801

    Article  CAS  Google Scholar 

  25. Thankachan, A.P., Sindhu, K.S., Krishnan, K.K., and Anilkumar, G., RSC Adv., 2015, vol. 5, p. 32675. https://doi.org/10.1039/c5ra03869c

    Article  CAS  Google Scholar 

  26. Wong, Y.-C., Jayanth, T.T., and Cheng, C.-H., Org. Lett., 2006, vol. 8, p. 5613. https://doi.org/10.1021/ol062344l

    Article  CAS  PubMed  Google Scholar 

  27. Lan, M.-T., Wu, W.-Y., Huang, S.-H., Luo, K.-L., and Tsai, F.-Y., RSC Adv., 2011, vol. 1, p. 1751. https://doi.org/10.1039/c1ra00406a

    Article  CAS  Google Scholar 

  28. Ku, X., Huang, H., Jiang, H., and Liu, H., J. Comb. Chem., 2009, vol. 11, p. 338. https://doi.org/10.1021/cc800182q

    Article  PubMed  CAS  Google Scholar 

  29. Qu, X., Li, T., Zhu, Y., Sun, P., Yang, H., and Mao, J., Org. Biomol. Chem., 2011, vol. 9, p. 5043. https://doi.org/10.1039/c1ob05155e

    Article  CAS  PubMed  Google Scholar 

  30. Gujadhur, R.K., Bates, C.G., and Venkataraman, D., Org. Lett., 2001, vol. 3, p. 4315. https://doi.org/10.1021/ol0170105

    Article  CAS  PubMed  Google Scholar 

  31. Barros, O.S.d.R., Silva, F.R., and Nunes, V.L., J. Sulfur Chem., 2019, vol. 40, p. 9. https://doi.org/10.1080/17415993.2018.1519566

    Article  CAS  Google Scholar 

  32. Baig, R.B.N., Vaddula, B.R., Nadagouda, M.N., and Varma, R.S., Green Chem., 2015, vol. 17, p. 1243. https://doi.org/10.1039/c4gc02047b

    Article  CAS  Google Scholar 

  33. Bates, C.G., Gujadhur, R.K., and Venkataraman, D., Org. Lett., 2002, vol. 4, p. 2803. https://doi.org/10.1021/ol0264105

    Article  CAS  PubMed  Google Scholar 

  34. Kwong, F.Y. and Buchwald, S.L., Org. Lett., 2002, vol. 4, p. 3517. https://doi.org/10.1021/ol0266673

    Article  CAS  PubMed  Google Scholar 

  35. Kabir, M.S., Van Linn, M.L., Monte, A., and Cook, J.M., Org. Lett., 2008, vol. 10, p. 3363. https://doi.org/10.1021/ol801149n

    Article  CAS  PubMed  Google Scholar 

  36. Zhu, D., Xu, L., Wu, F., and Wan, B., Tetrahedron Lett., 2006, vol. 47, p. 5781. https://doi.org/10.1016/j.tetlet.2006.05.178

    Article  CAS  Google Scholar 

  37. Zhang, H., Cao, W., and Ma, D., Synth. Commun., 2007, vol. 37, p. 25. https://doi.org/10.1080/00397910600977533

    Article  CAS  Google Scholar 

  38. Deng, W., Zou, Y., Wang, Y.-F., Liu, L., and Guo, Q.-X., Synlett, 2004, vol. 2004, p. 1254. https://doi.org/10.1055/s-2004-825584

    Google Scholar 

  39. Prasad, D.J.C. and Sekar, G., Synthesis, 2010, vol. 2010, p. 79. https://doi.org/10.1055/s-0029-1217056

    Article  CAS  Google Scholar 

  40. Zong, C., Liu, J., Chen, S., Zeng, R., and Zou, J., Chin. J. Chem., 2014, vol. 32, p. 212. https://doi.org/10.1002/cjoc.201300830

    Article  CAS  Google Scholar 

  41. Chen, Y.-J. and Chen, H.-H., Org. Lett., 2006, vol. 8, p. 5609. https://doi.org/10.1021/ol062339h

    Article  CAS  PubMed  Google Scholar 

  42. Lv, X. and Bao, W., J. Org. Chem., 2007, vol. 72, p. 3863. https://doi.org/10.1021/jo070443m

    Article  CAS  PubMed  Google Scholar 

  43. Wong, K.-T., Ku, S.-Y., and Yen, F.-W., Tetrahedron Lett., 2007, vol. 48, p. 5051. https://doi.org/10.1016/j.tetlet.2007.05.094

    Article  CAS  Google Scholar 

  44. Haldón, E., Álvarez, E., Nicasio, M.C., and Pérez, P.J., Organometallics, 2009, vol. 28, p. 3815. https://doi.org/10.1021/om900119r

    Article  CAS  Google Scholar 

  45. Yang, H., Xi, C., Miao, Z., and Chen, R., Eur. J. Org. Chem., 2011, vol. 2011, p. 3353. https://doi.org/10.1002/ejoc.201100274

    Article  CAS  Google Scholar 

  46. Chen, Y.-A., Badsara, S.S., Tsai, W.-T., and Lee, C.-F., Synthesis, 2015, vol. 47, p. 181. https://doi.org/10.1055/s-0034-1379206

    CAS  Google Scholar 

  47. Tan, C.-M., Chen, G.S., Chen, C.-S., and Chern, J.-W., J. Chin. Chem. Soc., 2011, vol. 58, p. 94. https://doi.org/10.1002/jccs.201190064

    Article  CAS  Google Scholar 

  48. Thomas, A.M., Asha, S., Sindhu, K.S., and Anilkumar, G., Tetrahedron Lett., 2015, vol. 56, p. 6560. https://doi.org/10.1016/j.tetlet.2015.10.014

    Article  CAS  Google Scholar 

  49. Bagley, M.C., Dix, M.C., and Fusillo, V., Tetrahedron Lett., 2009, vol. 50, p. 3661. https://doi.org/10.1016/j.tetlet.2009.03.115

    Article  CAS  Google Scholar 

  50. Feng, Y., Zhao, X., Wang, J., Zheng, F., and Xu, H., Chin. J. Chem., 2009, vol. 27, p. 2423. https://doi.org/10.1002/cjoc.201090019

    Article  CAS  Google Scholar 

  51. Jogdand, N.R., Shingate, B.B., and Shingare, M.S., Tetrahedron Lett., 2009, vol. 50, p. 6092. https://doi.org/10.1016/j.tetlet.2009.08.064

    Article  CAS  Google Scholar 

  52. Liu, Y., Huang, B., Cao, X., Wu, D., and Wan, J.-P., RSC Adv., 2014, vol. 4, p. 37733. https://doi.org/10.1039/c4ra07187e

    Article  CAS  Google Scholar 

  53. Verma, A.K., Singh, J., and Chaudhary, R., Tetrahedron Lett., 2007, vol. 48, p. 7199. https://doi.org/10.1016/j.tetlet.2007.07.205

    Article  CAS  Google Scholar 

  54. Zheng, Y., Du, X., and Bao, W., Tetrahedron Lett., 2006, vol. 47, p. 1217. https://doi.org/10.1016/j.tetlet.2005.11.164

    Article  CAS  Google Scholar 

  55. Bao, W., Liu, Y., and Lv, X., Synthesis, 2008, vol. 2008, p. 1911. https://doi.org/10.1055/s-2008-1067082

    Article  CAS  Google Scholar 

  56. Kabir, M.S., Lorenz, M., Van Linn, M.L., Namjoshi, O.A., Ara, S., and Cook, J.M., J. Org. Chem., 2010, vol. 75, p. 3626. https://doi.org/10.1021/jo1004179

    Article  CAS  PubMed  Google Scholar 

  57. Feng, Y., Wang, H., Sun, F., Li, Y., Fu, X., and Jin, K., Tetrahedron, 2009, vol. 65, p. 9737. https://doi.org/10.1016/j.tet.2009.09.085

    Article  CAS  Google Scholar 

  58. Prasad, D.J.C., Naidu, A. B., and Sekar, G., Tetrahedron Lett., 2009, vol. 50, p. 1411. https://doi.org/10.1016/j.tetlet.2009.01.022

    Article  CAS  Google Scholar 

  59. Xu, H.-J., Zhao, X.-Y., Deng, J., Fu, Y., and Feng, Y.-S., Tetrahedron Lett., 2009, vol. 50, p. 434. https://doi.org/10.1016/j.tetlet.2008.11.029

    Article  CAS  Google Scholar 

  60. Wu, Y.-J. and He, H., Synlett, 2003, vol. 2003, p. 1789. https://doi.org/10.1055/s-2003-41407

    Article  CAS  Google Scholar 

  61. Sperotto, E., van Klink, G.P.M., de Vries, J.G., and van Koten, G., J. Org. Chem., 2008, vol. 73, p. 5625. https://doi.org/10.1021/jo800491k

    Article  CAS  PubMed  Google Scholar 

  62. Feng, Y.-S., Li, Y.-Y., Tang, L., Wu, W., and Xu, H.-J., Tetrahedron Lett., 2010, vol. 51, p. 2489. https://doi.org/10.1016/j.tetlet.2010.02.155

    Article  CAS  Google Scholar 

  63. Uyeda, C., Tan, Y., Fu, G.C., and Peters, J.C., J. Am. Chem. Soc., 2013, vol. 135, p. 9548. https://doi.org/10.1021/ja404050f

    Article  CAS  PubMed  Google Scholar 

  64. Buranaprasertsuk, P., Chang, J.W.W., Chavasiri, W., and Chan, P.W.H., Tetrahedron Lett., 2008, vol. 49, p. 2023. https://doi.org/10.1016/j.tetlet.2008.01.060

    Article  CAS  Google Scholar 

  65. Zeni, G., Tetrahedron Lett., 2005, vol. 46, p. 2647. https://doi.org/10.1016/j.tetlet.2005.02.102

    Article  CAS  Google Scholar 

  66. Kao, H.-L., Chen, C.-K., Wang, Y.-J., and Lee, C.-F., Eur. J. Org. Chem., 2011, vol. 2011, p. 1776. https://doi.org/10.1002/ejoc.201001667

    Article  CAS  Google Scholar 

  67. Kao, H.-L. and Lee, C.-F., Org. Lett., 2011, vol. 13, p. 5204. https://doi.org/10.1021/ol2020863

    Article  CAS  PubMed  Google Scholar 

  68. Huang, Y.-T., Tsai, W.-T., Badsara, S.S., Chan, C.-C., and Lee, C.-F., J. Chin. Chem. Soc., 2014, vol. 61, p. 967. https://doi.org/10.1002/jccs.201400027

    Article  CAS  Google Scholar 

  69. Panova, Y.S., Kashin, A.S., Vorobev, M.G., Degtyareva, E.S., and Ananikov, V.P., ACS Catal., 2016, vol. 6, p. 3637. https://doi.org/10.1021/acscatal.6b00337

    Article  CAS  Google Scholar 

  70. Ranu, B.C., Saha, A., and Jana, R., Adv. Synth. Catal., 2007, vol. 349, p. 2690. https://doi.org/10.1002/adsc.200700289

    Article  CAS  Google Scholar 

  71. Rout, L., Saha, P., Jammi, S., and Punniyamurthy, T., Eur. J. Org. Chem., 2008, vol. 2008, p. 640. https://doi.org/10.1002/ejoc.200700978

    Article  CAS  Google Scholar 

  72. Herrero, M.T., SanMartin, R., and Domínguez, E., Tetrahedron, 2009, vol. 65, p. 1500. https://doi.org/10.1016/j.tet.2008.11.062

    Article  CAS  Google Scholar 

  73. Carril, M., SanMartin, R., Domínguez, E., and Tellitu, I., Chem.: Eur. J., 2007, vol. 13, p. 5100. https://doi.org/10.1002/chem.200601737

    Article  CAS  Google Scholar 

  74. Xu, H.-J., Liang, Y.-F., Zhou, X.-F., and Feng, Y.-S., Org. Biomol. Chem., 2012, vol. 10, p. 2562. https://doi.org/10.1039/c2ob06795a

    Article  CAS  PubMed  Google Scholar 

  75. She, J., Jiang, Z., and Wang, Y., Tetrahedron Lett., 2009, vol. 50, p. 593. https://doi.org/10.1016/j.tetlet.2008.11.082

    Article  CAS  Google Scholar 

  76. Dubey, A.V., Gharat, S.B., and Vijay Kumar, A., ChemistrySelect, 2017, vol. 2, p. 4852. https://doi.org/10.1002/slct.201700684

    Article  CAS  Google Scholar 

  77. Schwab, R.S., Singh, D., Alberto, E.E., Piquini, P., Rodrigues, O.E.D., and Braga, A.L., Catal. Sci. Technol., 2011, vol. 1, p. 569. https://doi.org/10.1039/c1cy00091h

    Article  CAS  Google Scholar 

  78. Jammi, S., Sakthivel, S., Rout, L., Mukherjee, T., Mandal, S., Mitra, R., Saha, P., and Punniyamurthy, T., J. Org. Chem., 2009, vol. 74, p. 1971. https://doi.org/10.1021/jo8024253

    Article  CAS  PubMed  Google Scholar 

  79. Rout, L., Sen, T.K., and Punniyamurthy, T., Angew. Chem. Int. Ed., 2007, vol. 46, p. 5583. https://doi.org/10.1002/anie.200701282

    Article  CAS  Google Scholar 

  80. Xu, H.-J., Zhao, X.-Y., Fu, Y., and Feng, Y.-S., Synlett, 2008, vol. 2008, p. 3063. https://doi.org/10.1055/s-0028-1087342

    Article  CAS  Google Scholar 

  81. Chen, W., Liu, X., Li, H., Fan, Z., Zheng, B., Weng, Z., Lai, Z., and Huang, K.-W., J. Mol. Engin. Mater., 2015, vol. 03, p. 1540001. https://doi.org/10.1142/s2251237315400018

    Article  CAS  Google Scholar 

  82. Swapna, K., Murthy, S.N., Jyothi, M.T., and Nageswar, Y.V.D., Org. Biomol. Chem., 2011, vol. 9, p. 5989. https://doi.org/10.1039/c1ob05597f

    Article  CAS  PubMed  Google Scholar 

  83. Babu, S.G. and Karvembu, R., Tetrahedron Lett., 2013, vol. 54, p. 1677. https://doi.org/10.1016/j.tetlet.2013.01.063

    Article  CAS  Google Scholar 

  84. Islam, S.M., Salam, N., Mondal, P., Roy, A.S., Ghosh, K., and Tuhina, K., J. Mol. Catal. A: Chem., 2014, vol. 387, p. 7. https://doi.org/10.1016/j.molcata.2014.02.007

    Article  CAS  Google Scholar 

  85. Rezaei, N. and Movassagh, B., Tetrahedron Lett., 2016, vol. 57, p. 1625. https://doi.org/10.1016/j.tetlet.2016.03.005

    Article  CAS  Google Scholar 

  86. Mondal, J., Modak, A., Dutta, A., and Bhaumik, A., Dalton Trans., 2011, vol. 40, p. 5228. https://doi.org/10.1039/c0dt01771j

    Article  CAS  PubMed  Google Scholar 

  87. Khodaei, M.M., Bahrami, K., and Meibodi, F.S., Appl. Organomet. Chem., 2017, vol. 31, p. e3714. https://doi.org/10.1002/aoc.3714

    Article  CAS  Google Scholar 

  88. Cabrero-Antonino, J.R., García, T., Rubio-Marqués, P., Vidal-Moya, J.A., Leyva-Pérez, A., Al-Deyab, S.S., Al-Resayes, S.I., Díaz, U., and Corma, A., ACS Catal., 2011, vol. 1, p. 147. https://doi.org/10.1021/cs100086y

    Article  CAS  Google Scholar 

  89. Veerakumar, P., Velayudham, M., Lu, K.-L., and Rajagopal, S., Catal. Sci. Technol., 2011, vol. 1, p. 1512. https://doi.org/10.1039/c1cy00300c

    Article  CAS  Google Scholar 

  90. Baig, R.B.N. and Varma, R.S., Chem. Commun., 2012, vol. 48, p. 2582. https://doi.org/10.1039/c2cc17283f

    Article  CAS  Google Scholar 

  91. Bhadra, S., Sreedhar, B., and Ranu, B.C., Adv. Synth. Catal., 2009, vol. 351, p. 2369. https://doi.org/10.1002/adsc.200900358

    Article  CAS  Google Scholar 

  92. Woo, H., Mohan, B., Heo, E., Park, J.C., Song, H., and Park, K.H., Nanoscale Res. Lett., 2013, vol. 8, p. 390. https://doi.org/10.1186/1556-276x-8-390

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  93. Chen, C.-K., Chen, Y.-W., Lin, C.-H., Lin, H.-P., and Lee, C.-F., Chem. Commun., 2010, vol. 46, p. 282. https://doi.org/10.1039/b918117b

    Article  CAS  Google Scholar 

  94. Kamal, A., Srinivasulu, V., Murty, J.N.S.R.C., Shankaraiah, N., Nagesh, N., Srinivasa Reddy, T., and Subba Rao, A.V., Adv. Synth. Catal., 2013, vol. 355, p. 2297. https://doi.org/10.1002/adsc.201300416

    Article  CAS  Google Scholar 

  95. Mallick, S., Rana, S., and Parida, K., Dalton Trans., 2011, vol. 40, p. 9169. https://doi.org/10.1039/c1dt10951k

    Article  CAS  PubMed  Google Scholar 

  96. Gonzalez-Arellano, C., Luque, R., and Macquarrie, D.J., Chem. Commun., 2009, vol. p. 1410. https://doi.org/10.1039/b818767c

    Google Scholar 

  97. Sharma, R.K., Gaur, R., Yadav, M., Rathi, A.K., Pechousek, J., Petr, M., Zboril, R., and Gawande, M.B., ChemCatChem, 2015, vol. 7, p. 3495. https://doi.org/10.1002/cctc.201500546

    Article  CAS  Google Scholar 

  98. Frindy, S., el Kadib, A., Lahcini, M., Primo, A., and García, H., ChemCatChem, 2015, vol. 7, p. 3307. https://doi.org/10.1002/cctc.201500565

    Article  CAS  Google Scholar 

  99. Kovács, S. and Novák, Z., Org. Biomol. Chem., 2011, vol. 9, p. 711. https://doi.org/10.1039/c0ob00397b

    Article  PubMed  Google Scholar 

  100. Mitrofanov, A.Y., Murashkina, A.V., Martín-García, I., Alonso, F., and Beletskaya, I.P., Catal. Sci. Technol., 2017, vol. 7, p. 4401. https://doi.org/10.1039/c7cy01343d

    Article  CAS  Google Scholar 

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The work was financially supported by the Russian Science Foundation (project no. 19-73-00168).

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Correspondence to I. P. Beletskaya.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1647–1659.

For communication I, see [1].

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Murashkina, A.V., Mitrofanov, A.Y. & Beletskaya, I.P. Copper in Cross-Coupling Reactions: II. Arylation of Thiols. Russ J Org Chem 55, 1629–1641 (2019). https://doi.org/10.1134/S1070428019110010

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