Full Paper
doi.org/10.1002/chem.202100342
Chemistry—A European Journal
28, 2561–2564; f) J. Yang, J. Xiao, T. Chen, S.-F. Yin, L.-B. Han, Chem.
Commun. 2016, 52, 12233–12236.
[19] a) M. Tobisu, K. Nakamura, N. Chatani, J. Am. Chem. Soc. 2014, 136,
5587–5590; b) J. Hu, Y. Zhao, J. Liu, Y. Zhang, Z. Shi, Angew. Chem. Int.
Ed. 2016, 55, 8718–8722; Angew. Chem. 2016, 128, 8860–8864; c) H.
Zhang, S. Hagihara, K. Itami, Chem. Eur. J. 2015, 21, 16796–16800; d) J.
Hu, H. Sun, W. Cai, X. Pu, Y. Zhang, Z. Shi, J. Org. Chem. 2016, 81, 14–24;
e) Z.-C. Cao, X.-L. Li, Q.-Y. Luo, H. Fang, Z.-J. Shi, Org. Lett. 2018, 20,
1995–1998.
[5] a) G. H. Posner, The Chemistry of Sulfones and Sulfoxides, ed. S. Patai, Z.
Rappoport and C. J. M. Stirling, Wiley, New York, 1988; b) Organic Sulfur
Chemistry: Structure and Mechanism, S. Oae, Ed., CRC Press: Boca Raton,
1991; c) Organic Sulfur Chemistry: Biochemical Aspects, S. Oae, T.
Okuyama, Eds., CRC Press: Boca Raton, 1992; d) A. Kalir, H. H. Kalir, The
Chemistry of Sulfur-Containing Functional Groups, ed. S. Patai and Z.
Rappoport, Wiley, New York, 1993; e) E. Block, Advances in Sulfur
Chemistry, JAI Press: Greenwich, 1994; f) R. J. Cremlyn, An Introduction of
Organosulfur Chemistry, Wiley: Chichester, 1996.
[6] a) M. C. Carreno, Chem. Rev. 1995, 95, 1717–1760; b) I. Fernández, N.
Khiar, Chem. Rev. 2003, 103, 3651–3706; c) T. Jia, M. Zhang, S. P.
McCollom, A. Bellomo, S. Montel, J. Mao, S. D. Dreher, C. J. Welch, E. L.
Regalado, R. T. Williamson, B. C. Manor, N. C. Tomson, P. J. Walsh, J. Am.
Chem. Soc. 2017, 139, 8337–8345.
[20] a) X. Pu, J. Hu, Y. Zhao, Z. Shi, ACS Catal. 2016, 6, 6692–6698; b) L. Guo,
M. Rueping, Chem. Eur. J. 2016, 22, 16787–16790.
[21] a) T. Schaub, U. Radius, Chem. Eur. J. 2005, 11, 5024–5030; b) T. Schaub,
M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964–15965; c) T.
Schaub, C. Döring, U. Radius, Dalton Trans. 2007, 1993–2002; d) T.
Schaub, M. Backes, U. Radius, Eur. J. Inorg. Chem. 2008, 2680–2690; e) T.
Schaub, P. Fischer, A. Steffen, T. Braun, U. Radius, A. Mix, J. Am. Chem.
Soc. 2008, 130, 9304–9317; f) T. Zell, M. Feierabend, B. Halfter, U. Radius,
J. Organomet. Chem. 2011, 696, 1380–1387; g) T. Schaub, P. Fischer, T.
Meins, U. Radius, Eur. J. Inorg. Chem. 2011, 3122–3126; h) T. Zell, U.
Radius, Z. Anorg. Allg. Chem. 2011, 637, 1858–1862; i) P. Fischer, K. Götz,
A. Eichhorn, U. Radius, Organometallics 2012, 31, 1374–1383; j) T. Zell, P.
Fischer, D. Schmidt, U. Radius, Organometallics 2012, 31, 5065–5073;
k) T. Zell, U. Radius, Z. Allg. Anorg. Chem. 2013, 639, 334–339; l) J. Zhou,
J. H. J. Berthel, A. Friedrich, T. B. Marder, U. Radius, J. Org. Chem. 2016,
81, 5789–5794.
[7] S. R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 2005, 44, 7674–7684;
Angew. Chem. 2005, 117, 7848–7859.
[8] a) E. Wenkert, T. W. Ferreira, E. L. Michelotti, J. Chem. Soc. Chem.
Commun. 1979, 637–638; b) C. I. Someya, M. Weidauer, S. Enthaler,
Catal. Lett. 2013, 143, 424–431.
[9] K. Yamamoto, S. Otsuka, K. Nogi, H. Yorimitsu, ACS Catal. 2017, 7, 7623–
7628.
[10] T. Schaub, M. Backes, U. Radius, Chem. Commun. 2007, 2037–2039.
[11] T. Schaub, M. Backes, O. Plietzsch, U. Radius, Dalton Trans. 2009, 7071–
7079.
[12] a) D. G. Hall, Boronic Acids: Preparation and Applications in Organic
Synthesis, Medicine and Materials, 2nd ed., Ed.: D. G. Hall, Wiley-VCH,
Weinheim, 2011; b) E. C. Neeve, S. J. Geier, I. A. I. Mkhalid, S. A. Westcott,
T. B. Marder, Chem. Rev. 2016, 116, 9091–9161.
[22] a) J. Zhou, M. W. Kuntze-Fechner, R. Bertermann, U. S. D. Paul, J. H. J.
Berthel, A. Friedrich, Z. Du, T. B. Marder, U. Radius, J. Am. Chem. Soc.
2016, 138, 5250–5253; b) Y.-M. Tian, X.-N. Guo, M. W. Kuntze-Fechner, I.
Krummenacher, H. Braunschweig, U. Radius, A. Steffen, T. B. Marder, J.
Am. Chem. Soc. 2018, 140, 17612–17623.
[23] L. Kuehn, D. G. Jammal, K. Lubitz, T. B. Marder, U. Radius, Chem. Eur. J.
2019, 25, 9514–9521.
[13] a) C. Sandford, V. K. Aggarwal, Chem. Commun. 2017, 53, 5481–5494;
b) A. B. Cuenca, R. Shishido, H. Ito, E. Fernández, Chem. Soc. Rev. 2017,
46, 415–430; c) A. Issaian, K. N. Tu, S. A. Blum, Acc. Chem. Res. 2017, 50,
2598–2609; d) D. Leonori, V. K. Aggarwal, Angew. Chem. Int. Ed. 2015,
54, 1082–1096; Angew. Chem. 2015, 127, 1096–1111; e) N. Miyaura, Bull.
Chem. Soc. Jpn. 2008, 81, 1535–1553; f) N. Miyaura, T. Yanagi, A. Suzuki,
Synth. Commun. 1981, 11, 513–519; g) N. Miyaura, A. Suzuki, Chem. Rev.
1995, 95, 2457–2483; h) A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722–
6737; Angew. Chem. 2011, 123, 6854–6869; i) A. J. J. Lennox, G. C. Lloyd-
Jones, Chem. Soc. Rev. 2014, 43, 412–443.
[14] a) I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig,
Chem. Rev. 2010, 110, 890–931; b) J. F. Hartwig, Chem. Soc. Rev. 2011,
40, 1992–2002; c) J. F. Hartwig, Acc. Chem. Res. 2012, 45, 864–873; d) A.
Ros, R. Fernández, J. M. Lassaletta, Chem. Soc. Rev. 2014, 43, 3229–3243;
e) F. W. Friese, A. Studer, Chem. Sci. 2019, 10, 8503–8518; f) Z. Kuang, K.
Yang, Y. Zhou, Q. Song, Chem. Commun. 2020, 56, 6469–6479; g) M.
Wang, Z. Shi, Chem. Rev. 2020, 120, 7348–7398.
[15] a) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508–
7510; b) W. Zhu, D. Ma, Org. Lett. 2006, 8, 261–263; c) C. Kleeberg, L.
Dang, Z. Lin, T. B. Marder, Angew. Chem. Int. Ed. 2009, 48, 5350–5354;
Angew. Chem. 2009, 121, 5454–5458; d) S. K. Bose, T. B. Marder, Org.
Lett. 2014, 16, 4562–4565; e) S. K. Bose, A. Deißenberger, A. Eichhorn,
P. G. Steel, Z. Lin, T. B. Marder, Angew. Chem. Int. Ed. 2015, 54, 11843–
11847; Angew. Chem. 2015, 127, 12009–12014; f) W. N. Palmer, J. V.
Obligacion, I. Pappas, P. J. Chirik, J. Am. Chem. Soc. 2016, 138, 766–769;
g) T. Yoshida, L. Ilies, E. Nakamura, ACS Catal. 2017, 7, 3199–3203; h) W.
Yao, H. Fang, S. Peng, H. Wen, L. Zhang, A. Hu, Z. Huang, Organo-
metallics 2016, 35, 1559–1564; i) P. K. Verma, S. Mandal, K. Geetharani,
ACS Catal. 2018, 8, 4049–4054; j) L. Kuehn, M. Huang, U. Radius, T. B.
Marder, Org. Biomol. Chem. 2019, 17, 6601–6606.
[24] Y.-M. Tian, X.-N. Guo, Z. Wu, A. Friedrich, S. A. Westcott, H. Braunsch-
weig, U. Radius, T. B. Marder, J. Am. Chem. Soc. 2020, 142, 13136–13144.
[25] a) Y. Uetake, T. Niwa, T. Hosoya, Org. Lett. 2016, 18, 2758–2761; b) M.
Bhanuchandra, A. Baralle, S. Otsuka, K. Nogi, H. Yorimitsu, A. Osuka, Org.
Lett. 2016, 18, 2966–2969.
[26] H. Saito, K. Nogi, H. Yorimitsu, Synthesis 2017, 49, 4769–4774.
[27] a) H. Minami, S. Otsuka, K. Nogi, H. Yorimitsu, ACS Catal. 2018, 8, 579–
583; b) C. Huang, J. Feng, R. Ma, S. Fang, T. Lu, W. Tang, D. Du, J. Gao,
Org. Lett. 2019, 21, 9688–9692.
[28] a) F. J. Lawlor, N. C. Norman, N. L. Pickett, E. G. Robins, P. Nguyen, G.
Lesley, T. B. Marder, J. A. Ashmore, J. C. Green, Inorg. Chem. 1998, 37,
5282–5288; b) P. Nguyen, G. Lesley, N. J. Taylor, T. B. Marder, N. L.
Pickett, W. Clegg, M. R. J. Elsegood, N. C. Norman, Inorg. Chem. 1994, 33,
4623–4624.
[29] a) G. Wang, H. Zhang, J. Zhao, W. Li, J. Cao, C. Zhu, S. Li, Angew. Chem.
Int. Ed. 2016, 55, 5985–5989; Angew. Chem. 2016, 128, 6089–6093; b) F.
Takahashi, K. Nogi, H. Yorimitsu, Eur. J. Org. Chem. 2020, 20, 3009–3012.
[30] a) S. C. Söderman, A. L. Schwan, Org. Lett. 2016, 13, 4192–4195; b) T. Jia,
M. Zhang, H. Jiang, C. Y. Wang, P. J. Walsh, J. Am. Chem. Soc. 2015, 137,
13887–13893.
supplementary crystallographic data for this paper. These data are
provided free of charge by the joint Cambridge Crystallographic Data
Centre and Fachinformationszentrum Karlsruhe Access Structures
[32] a) S. Ge, R. A. Green, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 1617–
1627; b) A. A. Danopoulos, T. Simler, P. Braunstein, Chem. Rev. 2019,
119, 3730–3961; c) V. Ritleng, M. Henrion, M. J. Chetcuti, ACS Catal.
2016, 6, 890–906.
[16] a) D. A. Wilson, C. J. Wilson, C. Moldoveanu, A. M. Resmerita, P.
Corcoran, L. M. Hoang, B. M. Rosen, V. Percec, J. Am. Chem. Soc. 2010,
132, 1800–1801; b) T. Yamamoto, T. Morita, J. Takagi, T. Yamakawa, Org.
Lett. 2011, 13, 5766–5769; c) G. A. Molander, L. N. Cavalcanti, C. García-
García, J. Org. Chem. 2013, 78, 6427–6439.
[17] a) X.-W. Liu, J. Echavarren, C. Zarate, R. Martin, J. Am. Chem. Soc. 2015,
137, 12470–12473; b) T. Niwa, H. Ochiai, Y. Watanabe, T. Hosoya, J. Am.
Chem. Soc. 2015, 137, 14313–14318; c) A. M. Christian, J. R. Bour, S. R.
Laursen, M. S. Sanford, J. Am. Chem. Soc. 2019, 141, 17322–17330.
[18] a) C. Zarate, R. Manzano, R. Martin, J. Am. Chem. Soc. 2015, 137, 6754–
6757; b) M. Tobisu, J. Zhao, H. Kinuta, T. Furukawa, T. Igarashi, N.
Chatani, Adv. Synth. Catal. 2016, 358, 2417–2421.
[33] M. S. Cheung, F. K. Sheong, T. B. Marder, Z. Lin, Chem. Eur. J. 2015, 21,
7480–7488.
[34] H. Saijo, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc. 2014, 136, 15158–
15161.
[35] a) R. H. Holm, P. Kennepohl, E. I. Solomon, Chem. Rev. 1996, 96, 2239–
2314; b) M. Alfano, C. Cavazza, Protein Sci. 2020, 29, 1071–1089.
Manuscript received: January 28, 2021
Accepted manuscript online: April 14, 2021
Version of record online: ■■■, ■■■■
Chem. Eur. J. 2021, 27, 1–11
10
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
��
These are not the final page numbers!