Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2022; 33(12): 1154-1179
DOI: 10.1055/a-1390-9065
DOI: 10.1055/a-1390-9065
cluster
Organic Photoredox Catalysis in Synthesis – Honoring Prof. Shunichi Fukuzumi’s 70th Birthday
Photophysical Properties and Redox Potentials of Photosensitizers for Organic Photoredox Transformations
We thank the National Science Foundation (grant number CHE-1846831) and the Welch Foundation (grant number E-1887) for funding our group’s research on organometallic photosensitizers and photoredox catalysis.
Abstract
Photoredox catalysis has proven to be a powerful tool in synthetic organic chemistry. The rational design of photosensitizers with improved photocatalytic performance constitutes a major advancement in photoredox organic transformations. This review summarizes the fundamental ground-state and excited-state photophysical and electrochemical attributes of molecular photosensitizers, which are important determinants of their photocatalytic reactivity.
Key words
photosensitizers - photoredox catalysis - redox potentials - excited states - photophysics - photochemistryPublication History
Received: 22 January 2021
Accepted: 15 February 2021
Accepted Manuscript online:
15 February 2021
Article published online:
23 March 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Inoue T, Fujishima A, Konishi S, Honda K. Nature 1979; 277: 637
- 2 Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
- 3 Lin W, Frei H. J. Am. Chem. Soc. 2005; 127: 1610
- 4 Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
- 5 Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 6 Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
- 7 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 8 Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
- 9 Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
- 10 Ischay MA, Ament MS, Yoon TP. Chem. Sci. 2012; 3: 2807
- 11 Nakajima M, Fava E, Loescher S, Jiang Z, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 8828
- 12 Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
- 13 Michelin C, Hoffmann N. ACS Catal. 2018; 8: 12046
- 14 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 15 Amos SG. E, Garreau M, Buzzetti L, Waser J. Beilstein J. Org. Chem. 2020; 16: 1163
- 16 Nicewicz DA, Nguyen TM. ACS Catal. 2014; 4: 355
- 17 Sato S, Arai T, Morikawa T, Uemura K, Suzuki TM, Tanaka H, Kajino T. J. Am. Chem. Soc. 2011; 133: 15240
- 18 Higashida S, Harada A, Kawakatsu R, Fujiwara N, Matsumura M. Chem. Commun. 2006; 2804
- 19 Qi M.-Y, Li Y.-H, Anpo M, Tang Z.-R, Xu Y.-J. ACS Catal. 2020; 10: 14327
- 20 Hockin BM, Li C, Robertson N, Zysman-Colman E. Catal. Sci. Technol. 2019; 9: 889
- 21 Pi Y, Feng X, Song Y, Xu Z, Li Z, Lin W. J. Am. Chem. Soc. 2020; 142: 10302
- 22 Dhakshinamoorthy A, Li Z, Garcia H. Chem. Soc. Rev. 2018; 47: 8134
- 23 Deng X, Li Z, García H. Chem. Eur. J. 2017; 23: 11189
- 24 Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, von Zelewsky A. Coord. Chem. Rev. 1988; 84: 85
- 25 Teegardin K, Day JI, Chan J, Weaver J. Org. Process Res. Dev. 2016; 20: 1156
- 26 Monos, T. M.; Stephenson, C. R. J. In Iridium(III) in Optoelectronic and Photonics Applications; Zysman-Colman, E., Ed.; Wiley: Hoboken, 2017, 541.
- 27 Zeitler, K. In Visible Light Photocatalysis in Organic Chemistry; Chap. 6, Stephenson, C. R. J.; Yoon, T. P.; MacMillan, D. W. C., Ed.; Wiley-VCH: Weinheim, 2018, 159.
- 28 Glaser F, Wenger OS. Coord. Chem. Rev. 2020; 405: 213129
- 29 Shon J.-H, Teets TS. Comments Inorg. Chem. 2020; 40: 53
- 30 Shon J.-H, Teets TS. ACS Energy Lett. 2019; 4: 558
- 31 Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
- 32 Roth HG, Romero NA, Nicewicz DA. Synlett 2016; 27: 714
- 33 Buzzetti L, Crisenza GE. M, Melchiorre P. Angew. Chem. Int. Ed. 2019; 58: 3730
- 34 Radwan YK, Maity A, Teets TS. Inorg. Chem. 2015; 54: 7122
- 35 Shon J.-H, Sittel S, Teets TS. ACS Catal. 2019; 9: 8646
- 36 Baik M.-H, Friesner RA. J. Phys. Chem. A 2002; 106: 7407
- 37 Fu Y, Liu L, Yu H.-Z, Wang Y.-M, Guo Q.-X. J. Am. Chem. Soc. 2005; 127: 7227
- 38 Silva-Junior MR, Schreiber M, Sauer SP. A, Thiel W. J. Chem. Phys. 2008; 129: 104103
- 39 Elgrishi N, Rountree KJ, McCarthy BD, Rountree ES, Eisenhart TT, Dempsey JL. J. Chem. Educ. 2018; 95: 197
- 40 Yang C, Mehmood F, Lam TL, Chan SL.-F, Wu Y, Yeung C.-S, Guan X, Li K, Chung CY.-S, Zhou C.-Y, Zou T, Che C.-M. Chem. Sci. 2016; 7: 3123
- 41 Espinoza EM, Clark JA, Soliman J, Derr JB, Morales M, Vullev VI. J. Electrochem. Soc. 2019; 166: H3175
- 42 Till NA, Tian L, Dong Z, Scholes GD, MacMillan DW. C. J. Am. Chem. Soc. 2020; 142: 15830
- 43 Connelly NG, Geiger WE. Chem. Rev. 1996; 96: 877
- 44 Pavlishchuk VV, Addison AW. Inorg. Chim. Acta 2000; 298: 97
- 45 Jones Jr WE, Fox MA. J. Phys. Chem. 1994; 98: 5095
- 46 Pellegrin Y, Odobel F. C. R. Chim. 2017; 20: 283
- 47 Murakami M, Ohkubo K, Fukuzumi S. Chem. Eur. J. 2010; 16: 7820
- 48 Kavarnos GJ. Top. Curr. Chem. 1990; 156: 21
- 49 Sartor SM, McCarthy BG, Pearson RM, Miyake GM, Damrauer NH. J. Am. Chem. Soc. 2018; 140: 4778
- 50 Prasad Hari D, König B. Chem. Commun. 2014; 50: 6688
- 51 Shen T, Zhao Z.-G, Yu Q, Xu H.-JJ. Photochem. Photobiol. Chem. 1989; 47: 203
- 52 Lazarides T, McCormick T, Du P, Luo G, Lindley B, Eisenberg R. J. Am. Chem. Soc. 2009; 131: 9192
- 53 Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951
- 54 Lambert CR, Kochevar IE. Photochem. Photobiol. 1997; 66: 15
- 55 Ravelli D, Fagnoni M. ChemCatChem 2012; 4: 169
- 56 Fidaly K, Ceballos C, Falguières A, Veitia MS.-I, Guy A, Ferroud C. Green Chem. 2012; 14: 1293
- 57 März M, Kohout M, Neveselý T, Chudoba J, Prukała D, Niziński S, Sikorski M, Burdziński G, Cibulka R. Org. Biomol. Chem. 2018; 16: 6809
- 58 Suppan P. J. Chem. Soc. Faraday Trans. 1 1975; 71: 539
- 59 Loutfy RO, Loutfy RO. J. Phys. Chem. 1972; 76: 1650
- 60 Schweitzer C, Mehrdad Z, Noll A, Grabner E.-W, Schmidt R. Helv. Chim. Acta 2001; 84: 2493
- 61 Gollnick K, Held SJ. Photochem. Photobiol. A: Chem. 1993; 70: 135
- 62 Gollnick K, Held S, Mártire DO, Braslavsky SE. J. Photochem. Photobiol. A: Chem. 1992; 69: 155
- 63 Serpa C, Arnaut LG. J. Phys. Chem. A 2000; 104: 11075
- 64 Cervantes-González J, Vosburg DA, Mora-Rodriguez SE, Vázquez MA, Zepeda LG, Villegas Gómez C, Lagunas-Rivera S. ChemCatChem 2020; 12: 3811
- 65 Yamago S, Miyazoe H, Iida K, Yoshida J.-i. Org. Lett. 2000; 2: 3671
- 66 Ohkubo K, Fujimoto A, Fukuzumi S. J. Am. Chem. Soc. 2013; 135: 5368
- 67 Ohkubo K, Hirose K, Fukuzumi S. Chem. Eur. J. 2015; 21: 2855
- 68 Giacco TD, Baciocchi E, Lanzalunga O, Elisei F. Chem. Eur. J. 2001; 7: 3005
- 69 Fukuzumi S, Fujita M, Noura S, Ohkubo K, Suenobu T, Araki Y, Ito O. J. Phys. Chem. A 2001; 105: 1857
- 70 Ohkubo K, Suga K, Morikawa K, Fukuzumi S. J. Am. Chem. Soc. 2003; 125: 12850
- 71 Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2012; 42: 97
- 72 Ohkubo K, Kotani H, Fukuzumi S. Chem. Commun. 2005; 4520
- 73 Fukuzumi S, Kotani H, Ohkubo K, Ogo S, Tkachenko NV, Lemmetyinen H. J. Am. Chem. Soc. 2004; 126: 1600
- 74 Benniston AC, Harriman A, Li P, Rostron JP, van Ramesdonk HJ, Groeneveld MM, Zhang H, Verhoeven JW. J. Am. Chem. Soc. 2005; 127: 16054
- 75 Romero NA, Nicewicz DA. J. Am. Chem. Soc. 2014; 136: 17024
- 76 Joshi-Pangu A, Lévesque F, Roth HG, Oliver SF, Campeau L.-C, Nicewicz D, DiRocco DA. J. Org. Chem. 2016; 81: 7244
- 77 Wang Y, Haze O, Dinnocenzo JP, Farid S, Farid RS, Gould IR. J. Org. Chem. 2007; 72: 6970
- 78 Ishimatsu R, Matsunami S, Kasahara T, Mizuno J, Edura T, Adachi C, Nakano K, Imato T. Angew. Chem. 2014; 126: 7113
- 79 Kretzschmar A, Patze C, Schwaebel ST, Bunz UH. F. J. Org. Chem. 2015; 80: 9126
- 80 Lu J, Pattengale B, Liu Q, Yang S, Shi W, Li S, Huang J, Zhang J. J. Am. Chem. Soc. 2018; 140: 13719
- 81 Saget T, König B. Chem. Eur. J. 2020; 26: 7004
- 82 Garreau M, Le Vaillant F, Waser J. Angew. Chem. Int. Ed. 2019; 58: 8182
- 83 Ishimatsu R, Edura T, Adachi C, Nakano K, Imato T. Chem. Eur. J. 2016; 22: 4889
- 84 Speckmeier E, Fischer TG, Zeitler K. J. Am. Chem. Soc. 2018; 140: 15353
- 85 Rolka AB, Koenig B. Org. Lett. 2020; 22: 5035
- 86 I. Alarcon E, González-Béjar M, Montes-Navajas P, Garcia H, Lissi EA, Scaiano JC. Photochem. Photobiol. Sci. 2012; 11: 269
- 87 Treat NJ, Sprafke H, Kramer JW, Clark PG, Barton BE, Read de Alaniz J, Fors BP, Hawker CJ. J. Am. Chem. Soc. 2014; 136: 16096
- 88 Discekici EH, Treat NJ, Poelma SO, Mattson KM, Hudson ZM, Luo Y, Hawker CJ, Read de Alaniz J. Chem. Commun. 2015; 51: 11705
- 89 Pearson RM, Lim C.-H, McCarthy BG, Musgrave CB, Miyake GM. J. Am. Chem. Soc. 2016; 138: 11399
- 90 Huber JR, Mantulin WW. J. Am. Chem. Soc. 1972; 94: 3755
- 91 Miranda MA, Garcia H. Chem. Rev. 1994; 94: 1063
- 92 Theriot JC, Lim C.-H, Yang H, Ryan MD, Musgrave CB, Miyake GM. Science 2016; 352: 1082
- 93 Du Y, Pearson RM, Lim C.-H, Sartor SM, Ryan MD, Yang H, Damrauer NH, Miyake GM. Chem. Eur. J. 2017; 23: 10962
- 94 Lim C.-H, Ryan MD, McCarthy BG, Theriot JC, Sartor SM, Damrauer NH, Musgrave CB, Miyake GM. J. Am. Chem. Soc. 2017; 139: 348
- 95 Luan Z.-H, Qu J.-P, Kang Y.-B. J. Am. Chem. Soc. 2020; 142: 20942
- 96 Buss BL, Beck LR, Miyake GM. Polym. Chem. 2018; 9: 1658
- 97 Marchini M, Gualandi A, Mengozzi L, Franchi P, Lucarini M, Cozzi PG, Balzani V, Ceroni P. Phys. Chem. Chem. Phys. 2018; 20: 8071
- 98 Ramanan C, Smeigh AL, Anthony JE, Marks TJ, Wasielewski MR. J. Am. Chem. Soc. 2012; 134: 386
- 99 Lee SK, Zu Y, Herrmann A, Geerts Y, Müllen K, Bard AJ. J. Am. Chem. Soc. 1999; 121: 3513
- 100 Ghosh I, Ghosh T, Bardagi JI, König B. Science 2014; 346: 725
- 101 Mei L, Veleta JM, Gianetti TL. J. Am. Chem. Soc. 2020; 142: 12056
- 102 Sørensen TJ, Nielsen MF, Laursen BW. ChemPlusChem 2014; 79: 1030
- 103 Hernández Delgado I, Pascal S, Wallabregue A, Duwald R, Besnard C, Guénée L, Nançoz C, Vauthey E, Tovar RC, Lunkley JL, Muller G, Lacour J. Chem. Sci. 2016; 7: 4685
- 104 Mei L, Gianetti T. Synlett 2021; 32: 337
- 105 Noto N, Koike T, Akita M. ACS Catal. 2019; 9: 4382
- 106 Noto N, Tanaka Y, Koike T, Akita M. ACS Catal. 2018; 8: 9408
- 107 Matsubara R, Yabuta T, Md Idros U, Hayashi M, Ema F, Kobori Y, Sakata K. J. Org. Chem. 2018; 83: 9381
- 108 Cybularczyk-Cecotka M, Szczepanik J, Giedyk M. Nat. Catal. 2020; 3: 872
- 109 Yabuta T, Hayashi M, Matsubara R. J. Org. Chem. 2021; 86: 2545
- 110 Mateos J, Rigodanza F, Vega-Peñaloza A, Sartorel A, Natali M, Bortolato T, Pelosi G, Companyó X, Bonchio M, Dell’Amico L. Angew. Chem. Int. Ed. 2020; 59: 1302
- 111 Hou M, Lin L, Chai X, Zhao X, Qiao B, Jiang Z. Chem. Sci. 2019; 10: 6629
- 112 Cao K, Tan SM, Lee R, Yang S, Jia H, Zhao X, Qiao B, Jiang Z. J. Am. Chem. Soc. 2019; 141: 5437
- 113 Zhao Y, Zhang C, Chin KF, Pytela O, Wei G, Liu H, Bureš F, Jiang Z. RSC Adv. 2014; 4: 30062
- 114 Liu Y, Chen Q, Tong Y, Ma Y. Macromolecules 2020; 53: 7053
- 115 Kim I, Park B, Kang G, Kim J, Jung H, Lee H, Baik M.-H, Hong S. Angew. Chem. Int. Ed. 2018; 57: 15517
- 116 Kim Y, Lee K, Mathi GR, Kim I, Hong S. Green Chem. 2019; 21: 2082
- 117 Moon Y, Park B, Kim I, Kang G, Shin S, Kang D, Baik M.-H, Hong S. Nat. Commun. 2019; 10: 4117
- 118 Liu D, Jiao M.-J, Feng Z.-T, Wang X.-Z, Xu G.-Q, Xu P.-F. Org. Lett. 2018; 20: 5700
- 119 Lee Y, Kwon MS. Eur. J. Org. Chem. 2020; 6028
- 120 Kalyanasundaram K. Coord. Chem. Rev. 1982; 46: 159
- 121 Juris A, Balzani V, Belser P, von Zelewsky A. Helv. Chim. Acta 1981; 64: 2175
- 122 Bock CR, Connor JA, Gutierrez AR, Meyer TJ, Whitten DG, Sullivan BP, Nagle JK. J. Am. Chem. Soc. 1979; 101: 4815
- 123 Young RC, Meyer TJ, Whitten DG. J. Am. Chem. Soc. 1976; 98: 286
- 124 Damrauer NH, Boussie TR, Devenney M, McCusker JK. J. Am. Chem. Soc. 1997; 119: 8253
- 125 Anderson BL, Maher AG, Nava M, Lopez N, Cummins CC, Nocera DG. J. Phys. Chem. B 2015; 119: 7422
- 126 Lowry MS, Hudson WR, Pascal RA, Bernhard S. J. Am. Chem. Soc. 2004; 126: 14129
- 127 Bernhard S, Barron JA, Houston PL, Abruña HD, Ruglovksy JL, Gao X, Malliaras GG. J. Am. Chem. Soc. 2002; 124: 13624
- 128 Haga M, Dodsworth ES, Eryavec G, Seymour P, Lever AB. P. Inorg. Chem. 1985; 24: 1901
- 129 Crutchley RJ, Lever AB. P. J. Am. Chem. Soc. 1980; 102: 7128
- 130 Rillema DP, Allen G, Meyer TJ, Conrad D. Inorg. Chem. 1983; 22: 1617
- 131 Nacsa ED, MacMillan DW. C. J. Am. Chem. Soc. 2018; 140: 3322
- 132 Dedeian K, Djurovich PI, Garces FO, Carlson G, Watts RJ. Inorg. Chem. 1991; 30: 1685
- 133 Nguyen JD, D’Amato EM, Narayanam JM. R, Stephenson CR. J. Nat. Chem. 2012; 4: 854
- 134 Tamayo AB, Alleyne BD, Djurovich PI, Lamansky S, Tsyba I, Ho NN, Bau R, Thompson ME. J. Am. Chem. Soc. 2003; 125: 7377
- 135 Singh A, Teegardin K, Kelly M, Prasad KS, Krishnan S, Weaver JD. J. Organomet. Chem. 2015; 776: 51
- 136 Kim H, Kim T, Lee DG, Roh SW, Lee C. Chem. Commun. 2014; 50: 9273
- 137 Pfund B, Steffen DM, Schreier MR, Bertrams M.-S, Ye C, Börjesson K, Wenger OS, Kerzig C. J. Am. Chem. Soc. 2020; 142: 10468
- 138 Guo X, Okamoto Y, Schreier MR, Ward TR, Wenger OS. Chem. Sci. 2018; 9: 5052
- 139 Kerzig C, Guo X, Wenger OS. J. Am. Chem. Soc. 2019; 141: 2122
- 140 Kim T, McCarver SJ, Lee C, MacMillan DW. C. Angew. Chem. Int. Ed. 2018; 57: 3488
- 141 Ochola JR, Wolf MO. Org. Biomol. Chem. 2016; 14: 9088
- 142 Ladouceur S, Zysman-Colman E. Eur. J. Inorg. Chem. 2013; 2985
- 143 Slinker JD, Gorodetsky AA, Lowry MS, Wang J, Parker S, Rohl R, Bernhard S, Malliaras GG. J. Am. Chem. Soc. 2004; 126: 2763
- 144 Choi GJ, Zhu Q, Miller DC, Gu CJ, Knowles RR. Nature 2016; 539: 268
- 145 Lu Z, Yoon TP. Angew. Chem. Int. Ed. 2012; 51: 10329
- 146 Lowry MS, Goldsmith JI, Slinker JD, Rohl R, Pascal RA, Malliaras GG, Bernhard S. Chem. Mater. 2005; 17: 5712
- 147 Simons RT, Scott GE, Kanegusuku AG, Roizen JL. J. Org. Chem. 2020; 85: 6380
- 148 Hanss D, Freys JC, Bernardinelli G, Wenger OS. Eur. J. Inorg. Chem. 2009; 4850
- 149 Takizawa S, Shimada K, Sato Y, Murata S. Inorg. Chem. 2014; 53: 2983
- 150 Shon J.-H, Teets TS. Inorg. Chem. 2017; 56: 15295
- 151 Lam TL, Lai J, Annapureddy RR, Xue M, Yang C, Guan Y, Zhou P, Chan SL.-F. Inorg. Chem. 2017; 56: 10835
- 152 Porras JA, Mills IN, Transue WJ, Bernhard S. J. Am. Chem. Soc. 2016; 138: 9460
- 153 Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem. Eur. J. 2012; 18: 7336
- 154 Kern J.-M, Sauvage J.-P. J. Chem. Soc., Chem. Commun. 1987; 546
- 155 Zheng L, Jiang Q, Bao H, Zhou B, Luo S.-P, Jin H, Wu H, Liu Y. Org. Lett. 2020; 22: 8888
- 156 Bao H, Zhou B, Luo S.-P, Xu Z, Jin H, Liu Y. ACS Catal. 2020; 10: 7563
- 157 Knorn M, Rawner T, Czerwieniec R, Reiser O. ACS Catal. 2015; 5: 5186
- 158 Alkan-Zambada M, Hu X. Organometallics 2018; 37: 3928 ; corrigendum: Organometallics 2020, 39, 1456
- 159 Michelet B, Deldaele C, Kajouj S, Moucheron C, Evano G. Org. Lett. 2017; 19: 3576
- 160 Minozzi C, Caron A, Grenier-Petel J.-C, Santandrea J, Collins SK. Angew. Chem. Int. Ed. 2018; 57: 5477
- 161 Caron A, Morin É, Collins SK. ACS Catal. 2019; 9: 9458
- 162 Wang C, Guo M, Qi R, Shang Q, Liu Q, Wang S, Zhao L, Wang R, Xu Z. Angew. Chem. Int. Ed. 2018; 57: 15841
- 163 Nitelet A, Thevenet D, Schiavi B, Hardouin C, Fournier J, Tamion R, Pannecoucke X, Jubault P, Poisson T. Chem. Eur. J. 2019; 25: 3262
- 164 Wang B, Shelar DP, Han X.-Z, Li T.-T, Guan X, Lu W, Liu K, Chen Y, Fu W.-F, Che C.-M. Chem. Eur. J. 2015; 21: 1184
- 165 Kober EM, Sullivan BP, Dressick WJ, Caspar JV, Meyer TJ. J. Am. Chem. Soc. 1980; 102: 7383
- 166 Ravetz BD, Tay NE. S, Joe CL, Sezen-Edmonds M, Schmidt MA, Tan Y, Janey JM, Eastgate MD, Rovis T. ACS Cent. Sci. 2020; 6: 2053
- 167 Sauvage JP, Collin JP, Chambron JC, Guillerez S, Coudret C, Balzani V, Barigelletti F, De Cola L, Flamigni L. Chem. Rev. 1994; 94: 993
- 168 Sasaki Y, Oshikawa M, Bharmoria P, Kouno H, Hayashi-Takagi A, Sato M, Ajioka I, Yanai N, Kimizuka N. Angew. Chem. Int. Ed. 2019; 58: 17827
- 169 Zhang Y, Petersen JL, Milsmann C. J. Am. Chem. Soc. 2016; 138: 13115
- 170 Zhang Y, Lee TS, Petersen JL, Milsmann C. J. Am. Chem. Soc. 2018; 140: 5934
- 171 Zhang Y, Petersen JL, Milsmann C. Organometallics 2018; 37: 4488
- 172 Herr P, Glaser F, Büldt LA, Larsen CB, Wenger OS. J. Am. Chem. Soc. 2019; 141: 14394
- 173 Büldt LA, Guo X, Prescimone A, Wenger OS. Angew. Chem. Int. Ed. 2016; 55: 11247
- 174 Büldt LA, Guo X, Vogel R, Prescimone A, Wenger OS. J. Am. Chem. Soc. 2017; 139: 985
- 175 Büldt LA, Wenger OS. Angew. Chem. Int. Ed. 2017; 56: 5676
- 176 Sattler W, Henling LM, Winkler JR, Gray HB. J. Am. Chem. Soc. 2015; 137: 1198
- 177 Sattler W, Ener ME, Blakemore JD, Rachford AA, LaBeaume PJ, Thackeray JW, Cameron JF, Winkler JR, Gray HB. J. Am. Chem. Soc. 2013; 135: 10614
- 178 Mann KR, Gray HB, Hammond GS. J. Am. Chem. Soc. 1977; 99: 306
- 179 Yu D, To W.-P, Tong GS. M, Wu L.-L, Chan K.-T, Du L, Phillips DL, Liu Y, Che C.-M. Chem. Sci. 2020; 11: 6370
- 180 Chan K.-T, Lam T.-L, Yu D, Du L, Phillips DL, Kwong C.-L, Tong GS. M, Cheng G, Che C.-M. Angew. Chem. Int. Ed. 2019; 58: 14896
- 181 Yeung K.-T, To W.-P, Sun C, Cheng G, Ma C, Tong GS. M, Yang C, Che C.-M. Angew. Chem. Int. Ed. 2017; 56: 133
- 182 Stevenson SM, Shores MP, Ferreira EM. Angew. Chem. Int. Ed. 2015; 54: 6506
- 183 McDaniel AM, Tseng H.-W, Damrauer NH, Shores MP. Inorg. Chem. 2010; 49: 7981
- 184 To W.-P, Tong GS.-M, Lu W, Ma C, Liu J, Chow AL.-F, Che C.-M. Angew. Chem. Int. Ed. 2012; 51: 2654
- 185 McTiernan CD, Morin M, McCallum T, Scaiano JC, Barriault L. Catal. Sci. Technol. 2015; 6: 201
- 186 Nzulu F, Telitel S, Stoffelbach F, Graff B, Morlet-Savary F, Lalevée J, Fensterbank L, Goddard J.-P, Ollivier C. Polym. Chem. 2015; 6: 4605
- 187 McCallum T, Barriault L. Chem. Sci. 2016; 7: 4754
- 188 Choi WJ, Choi S, Ohkubo K, Fukuzumi S, Cho EJ, You Y. Chem. Sci. 2015; 6: 1454
- 189 Zhong J.-J, Meng Q.-Y, Wang G.-X, Liu Q, Chen B, Feng K, Tung C.-H, Wu L.-Z. Chem. Eur. J. 2013; 19: 6443
- 190 Zhong J.-J, Yang C, Chang X.-Y, Zou C, Lu W, Che C.-M. Chem. Commun. 2017; 53: 8948
- 191 Yin H, Carroll PJ, Anna JM, Schelter EJ. J. Am. Chem. Soc. 2015; 137: 9234
- 192 Qiao Y, Schelter EJ. Acc. Chem. Res. 2018; 51: 2926
- 193 Yin H, Carroll PJ, Manor BC, Anna JM, Schelter EJ. J. Am. Chem. Soc. 2016; 138: 5984
- 194 Qiao Y, Cheisson T, Manor BC, Carroll PJ, Schelter EJ. Chem. Commun. 2019; 55: 4067
- 195 Yin H, Jin Y, Hertzog JE, Mullane KC, Carroll PJ, Manor BC, Anna JM, Schelter EJ. J. Am. Chem. Soc. 2016; 138: 16266
- 196 Qiao Y, Yang Q, Schelter EJ. Angew. Chem. Int. Ed. 2018; 57: 10999