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ARTICLE
S. Kim and K. M. Maloney, J. Am. CDhOemI: 1.0S.1o0c3.9,/D200S1C90,2194471E,
18416.
J. M. Baskin and Z. Wang, Tetrahedron Lett., 2002, 43, 8479.
J. J. Day, D. L. Neill, S. Xu and M. Xian, Org. Lett., 2017, 19,
3819.
For reviews on Rongalite, see: (a) S. Kotha and P. Khedkar,
Chem. Rev., 2012, 112, 1650. (b) S. Kotha, P. Khedkar and Y.
Dommaraju, Tetrahedron Lett., 2019, 60, 631. For related
examples, see: (c) W. Zhang and M. Luo, Chem. Commun.,
2016, 52, 2980. (d) A. Shavnya, S. B. Coffey, K. D. Hesp, S. C.
Ross and A. S. Tsai, Org. Lett., 2016, 18, 5848. (e) M. Wang, B.-
C. Tang, J.-G. Wang, J.-C. Xiang, A.-Y. Guan, P.-P. Huang, W.-Y.
Guo, Y.-D. Wu and A.-X. Wu, Chem. Commun., 2018, 54, 7641.
(f) E. M. Alvarez, M. B. Plutschack, F. Berger and T. Ritter, Org.
Lett., 2020, DOI: 10.1021/acs.orglett.0c00982. (f) X.-L. Chen,
B.-C. Tang, C. He, J.-T. Ma, S.-Y. Zhang, Y.-D. Wu and A.-W. Wu,
Chem. Commun., 2020, DOI: 10.1039/D0CC05800A.
Acknowledgements
Support for this research was provided by the National Research
Foundation (NRF) funded by the Ministry of Science and ICT of
Korea (2017R1A2B3002869 and 2020R1A2B5B03002271). H.-S.
Um gratefully acknowledges Seoul National University for
generous funding through SNU Fellowship for Fundamental
Academic Fields. This paper is dedicated to P. H. Dixneuf for his
outstanding contribution to organometallic chemistry and
catalysis.
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Notes and references
1
For reviews on the construction of C-S bonds, see: (a) T. Kondo
and T.-A. Mitsudo, Chem. Rev., 2000, 100, 3205. (b) N.-W. Liu,
S. Liang and G. Manolikakes, Synthesis, 2016, 48, 1939. (c) J.
Zhu, W.-C. Yang, X.-D. Wang and L. Wu, Adv. Synth. Catal.,
2018, 360, 386. For reviews on the utility of sulfonyl motifs,
see: (d) M. J. El-Hibri and S. A. Weinberg, in Encyclopedia of
Polymer Science and Technology, Jonn Wiley & Sons, New
York, 2002, vol. 4, pp. 1-26. (e) C. Dizman, M. A. Tasdelen and
Y. Yagci, Polym. Int., 2013, 62, 991. (f) M. Feng, B. Tang, S. H.
Liang and X. Jiang, Curr. Top. Med. Chem., 2016, 16, 1200. (g)
P. Devendar and G.-F. Yang, Top. Curr. Chem., 2017, 375, 82.
(h) K. A. Scott and J. T. Njardarson, Top. Curr. Chem., 2018,
376, 5. (i) B. M. Trost and C. A. Kalnmals, Chem. Eur. J., 2019,
25, 11193.
10 A. Shavnya, K. D. Hesp and A. S. Tsai, Adv. Synth. Catal., 2018,
360, 1768.
11 H.-S. Um, J. Min, T. An, J. Choi and C. Lee, Org. Chem. Front.,
2018, 5, 2158.
12 (a) N. Umierski and G. Manolikakes, Org. Lett., 2013, 15, 188.
(b) N. Umierski and G. Manolikakes, Org. Lett., 2013, 15, 4972.
(c) N. Margraf and G. Manolikakes, J. Org. Chem., 2015, 80,
2582.
13 H. Yang, Y. Li, M. Jiang, J. Wang and H. Fu, Chem. Eur. J., 2011,
17, 5662.
14 A. Rodríguez and W. J. Moran, J. Org. Chem., 2016, 81, 2543.
15 For examples of coupling between sulfinates and aryl halides
under copper catalysis, see: (a) J. M. Baskin and Z. Wang, Org.
Lett., 2002, 4, 4423. (b) W. Zhu and D. Ma, J. Org. Chem., 2005,
70, 2696. (c) M. Bian, F. Xu and C. Ma, Synthesis, 2007, 2951.
(d) Y.-Q. Yuan and S.-R. Guo, Synlett, 2011, 2750. (e) B. T. V.
Srinivas, V. S. Rawat, K. Konda and B. Sreedhar, Adv. Synth.
Catal., 2014, 356, 805. (f) M. Yang, H. Shen, Y. Li, C. Shen and
P. Zhang, RSC Adv., 2014, 4, 26295. (g) J. Zhao, S. Niu, X. Jiang,
Y. Jiang, X. Zhang, T. Sun and D. Ma, J. Org. Chem., 2018, 83,
6589.
16 For examples of coupling between sulfinates and aryl halides
under palladium catalysis, see: (a) S. Cacchi, G. Fabrizi, A.
Goggiamani and L. M. Parisi, Org. Lett., 2002, 4, 4719. (b) S.
Cacchi, G. Fabrizi, A. Goggiamani and L. M. Parisi, Synlett,
2003, 361. (c) S. Cacchi, G. Fabrizi, A. Goggiamani, L. M. Parisi
and R. Bernini, J. Org. Chem., 2004, 69, 5608. (d) L. A. Smyth,
E. M. Phillips, V. S. Chan, J. G. Napolitano, R. Henry and S.
Shekhar, J. Org. Chem., 2016, 81, 1285.
17 For examples of coupling between sulfinates and aryl halides
under nickel catalysis, see: N.-W. Liu, S. Liang, N. Margraf, S.
Shaaban, V. Luciano, M. Drost and G. Manolikakes, Eur. J. Org.
Chem., 2018, 1208.
18 For examples of coupling between sulfinates and aryl halides
under metal-free conditions, see: (a) K. M. Maloney, J. T.
Kuethe and K. Linn, Org. Lett., 2011, 13, 102. (b) S. Liang, R.-Y.
Zhang, L.-Y. Xi, S.-Y. Chen and X.-Q. Yu, J. Org. Chem., 2013,
78, 11874.
19 For examples of coupling between sulfinates and aryl halides
under photoredox catalysis, see: (a) H. Yue, C. Zhu and M.
Rueping, Angew. Chem. Int. Ed., 2018, 57, 1371. (b) N.-W. Liu,
K. Hofman, A. Herbert and G. Manolikakes, Org. Lett., 2018,
20, 760. (c) M. J. Cabrera-Afonso, Z.-P. Lu, C. B. Kelly, S. M.
Lang, R. Dykstra, O. Gutierrez and G. A. Molander, Chem. Sci.,
2018, 9, 3186.
20 For examples of coupling between sulfinates and aryl halides
under irradiation, see: L. Chen, J. Liang, Z.-Y. Chen, J. Chen, M.
Yan and X.-J. Zhang, Adv. Synth. Catal., 2019, 361, 956.
21 (a) J. J. Byerley and W. K. Teo, Can. J. Chem., 1969, 47, 3355.
(b) Z. Jusys and A. Vaškelis, Langmuir, 1992, 8, 1230. (c) D.
2
3
(a) S. D. Burke, in Encyclopedia of Reagents for Organic
Synthesis, ed. L. A. Paquette, John Wiley & Sons, Chichester,
1995, vol. 7, p. 4688. (b) P. Vogel, M. Turks, L. Bouchez, D.
Marković, A. Varela-Álvarez and J. Á. Sordo, Acc. Chem. Res.,
2007, 40, 931.
For a seminal report, see: (a) H. Woolven, C. González-
Rodríguez, I. Marco, A. L. Thomson and M. C. Willis, Org. Lett.,
2011, 13, 4876. For reviews on DABSO, see: (b) E. J. Emmett
and M. C. Willis, Asian J. Org. Chem., 2015, 4, 602. (c) M. C.
Willis, Phosphorus Sulfur Silicon Relat. Elem., 2019, 194, 654.
S. Ye, G. Qiu and J. Wu, Chem. Commun., 2019, 55, 1013.
(a) J. Zhang, K. Zhou, G. Qiu and J. Wu, Org. Chem. Front.,
2019, 6, 36. (b) Y. Li, T. Liu, G. Qiu and J. Wu, Adv. Synth. Catal.,
2019, 361, 1154. (c) Y. Meng, M. Wang and X. Jiang, Angew.
Chem. Int. Ed., 2020, 59, 1346.
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5
6
For reviews on sulfinates, see: (a) J. Aziz, S. Messaoudi, M.
Alami and A. Hamze, Org. Biomol. Chem., 2014, 12, 9743. (b)
D. Kaiser, I. Klose, R. Oost, J. Neuhaus and N. Maulide, Chem.
Rev., 2019, 119, 8701. For examples of sulfinate precursors in
a form of thiosulfonate, see: (c) D. H. R. Barton, B. Lacher, B.
Misterkiewicz and S. Z. Zard, Tetrahedron Lett., 1988, 44,
1153. (d) P. K. Shyam and H.-Y. Jang, J. Org. Chem., 2017, 82,
1761. (e) P. K. Shyam, S. Son and H.-Y. Jang, Eur. J. Org. Chem.,
2017, 5025. (f) S. Son, P. K. Shyam, H. Park, I. Jeong and H.-Y.
Jang, Eur. J. Org. Chem., 2018, 3365. For examples of sulfinate
precursors in a form of allyl sulfone, see: (g) G. Le Duc, E.
Bernoud, G. Prestat, S. Cacchi, G. Fabrizi, A. Iazzetti, D. Madec
and G. Poli, Synlett, 2011, 2943. For examples of sulfinate
precursors in a form of 2-pyridyl sulfone, see: (h) Y. Zhao, W.
Huang, L. Zhu and J. Hu, Org. Lett., 2010, 12, 1444. (i) Q. Zhou,
A. Ruffoni, R. Gianatassio, Y. Fujiwara, E. Sella, D. Shabat and
P. S. Baran, Angew. Chem. Int. Ed., 2013, 52, 3949. (j) Q. Zhou,
J. Gui, C.-M. Pan, E. Albone, X. Cheng, E. M. Suh, L. Grasso, Y.
Ishihara and P. S. Baran, J. Am. Chem. Soc., 2013, 135, 12994.
(k) R. Gianatassio, S. Kawamura, C. L. Eprile, K. Foo, J. Ge, A. C.
Burns, M. R. Collins and P. S. Baran, Angew. Chem. Int. Ed.,
2014, 53, 9851. For examples of sulfinate precursors in a form
of sulfonamide, see: (l) C. S. Richards-Taylor, D. C. Blackmore
and M. C. Willis, Chem. Sci., 2014, 5, 222. (m) P. S. Fier and K.
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