10.1002/adsc.202001250
Advanced Synthesis & Catalysis
[9] B. C. Austad, T. L. Calkins, C. E. Chase, F. G. Fang, T.
E. Horstmann, Y. Hu, B. M. Lewis, X. Niu, T. A.
Noland, J. D. Orr, M. J. Schnaderbeck, H. Zhang, N.
Asakawa, N. Asai, H. Chiba, T. Hasebe, Y. Hoshino, H.
Ishizuka, T. Kajima, A. Kayano, Y. Komatsu, M.
Kubota, H. Kuroda, M. Miyazawa, K. Tagami, T.
Watanabe, Synlett 2013, 24, 333-337.
12705-12709; b) J. L. Schwarz, R. Kleinmans, O.
Paulisch, F. Glorius, J. Am. Chem. Soc. 2020, 142,
2168-2174; c) J. L. Schwarz, H.-M. Huang, T. O.
Paulisch, F. Glorius, ACS Catal. 2020, 10, 1621-1627;
d) F. Schäfers, L. Quach, J. L. Schwarz, M. Saladrigas,
C. G. Daniliuc, F. Glorius, ACS Catal. 2020, 10,
11841–11847; e) H.-M. Huang, P. Bellotti, C. Daniliuc,
F. Glorius, Angew. Chem. Int. Ed. 2020, DOI:
org/10.1002/anie.202011996.
[10] M. Yan, Y. Kawamata, P. S. Baran, Chem. Rev. 2017,
117, 13230–13319.
[19] a) H. Mitsunuma, S. Tanabe, H. Fus, K. Ohkubo, M.
Kanai, Chem. Sci. 2019, 10, 3459-3465; b) S. Tanabe,
H. Mitsunuma, and M. Kanai, J. Am. Chem. Soc. 2020,
142, 28, 12374–12381.
[11] M. Durandetti, C. Meignein, J. Périchon, J. Org.
Chem. 2003, 68, 3121-3124.
[12] For selected reviews on photoredox catalysis, see: a)
K. Zeitler, Angew. Chem. Int. Ed. 2009, 48, 9785-9789;
Angew. Chem. 2009, 121, 9969-9974; b) T. P. Yoon, M.
A. Ischay, J. Du, Nat. Chem. 2010, 2, 527-532; c) J. M.
R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev.
2011, 40, 102-113; d) J. Xuan, W. Xiao, Angew. Chem.
2012, 124, 6934-6944; Angew. Chem. Int. Ed. 2012, 51,
6828-6838; e) L. Shi, W.-J. Xia, Chem. Soc. Rev. 2012,
41, 7687-7697; f) D. Ravelli, M. Fagnoni,
ChemCatChem 2012, 4, 169-171; g) C. K. Prier, D. A.
Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 7,
5322–5363; h) Y. Xi, H. Yi, A. Lei, Org. Biomol.
Chem. 2013, 11, 2387-2403; i) R. A. Angnes, Z. Li, C.
R. D. Correia, G. B. Hammond, Org. Biomol. Chem.
2015, 13, 9152-9167; j) Skubi, K. L.; Blum. T. R.;
Yoon, T. P. Chem. Rev. 2016, 116, 10035-10074; k) X.
Lang, J. Zhao, X.-d. Chen, Chem. Soc. Rev. 2016, 45,
3026-3038; l) S. P. Pitre, C. D. McTiernan, J. C.
Scaiano, Acc. Chem. Res. 2016, 49, 1320−1330; m) M.
H. Shaw, J. Twilton, D. W. C. MacMillan, J. Org.
Chem. 2016, 81, 6898–6926; n) N. A. Romero, D. A.
Nicewicz, Chem. Rev. 2016, 116, 10075−10166; o) M.
Parasram, V. Gevorgyan, Chem. Soc. Rev. 2017, 46,
6227-6240; p) K. N. Lee, M.-Y. Ngai, Chem. Commun.
2017, 53, 13093-13112; q) Y. – Q. Zou, F. M.
Hoermann, T. Bach, Chem. Soc. Rev. 2018, 47, 278-
290; r) L. Marzo, S. K. Pagire, O. Reiser, B. König,
Angew. Chem. Int. Ed. 2018; 57, 10034-10072; Agew.
Chem. 2018, 130, 10188-10228; s) C. B. Larsen, O. S.
Wenger, Chem. Eur. J. 2018, 24, 2039-2058; t) R. C.
McAtee, E. J. McClein, C. R. J. Stephenson, Trends in
Chem. 2019, 1, 111-125.
[20] A. Gualandi, G. Rodeghiero, A. Faraone, F. Patuzzo,
M. Marchini, F. Calogero, R. Perciaccante, T. P. Jansen,
P. Ceroni, P. G. Cozzi, Chem. Commun. 2019, 55,
6838-6841.
[21] For the synthesis and photophysical properties of the
organic dye 3DPAFIPN, see: E. Speckmeier, T. G.
Fischer, K. Zeitler, J. Am. Chem. Soc. 2018, 140,
15353-15356.
[22] a) A. Gualandi, F. Calogero, M. Mazzarini, S. Guazzi,
A. Fermi, G. Bergamini, P. G. Cozzi, ACS Catal. 2020,
10, 3857–3863; b) A. Fermi, A. Gualandi, G.
Bergamini, P. G. Cozzi, Eur. J. Org. Chem. 2020, doi:
10.1002/ejoc.202000966 For a redox cycle based on
stoichiometric reductant (Mn), see: R. E. Estévez, J.
Justicia, B. Bazdi, N. Fuentes, M. Paradas, D.
Choquesillo-Lazarte, J. M. García-Ruiz, R. Robles, A.
Gansäuer, J. M. Cuerva, J. E. Oltra, Chem. Eur. J. 2009,
12, 2774-2791.
[23] For the use of abundant and cheap cobalt in chemical
reactions, see: Cobalt Catalysis in Organic Synthesis:
Methods and Reactions, M. Hapke, G. Hilt (Eds),
Wiley-VCH, 2019.
[24] a) P. Gomes, C. Gosmini, J. Périchon, Synthesis 2003,
1909-1916; for the coupling of allylcobalt with various
alkyl halides, catalyzed by simple cobalt(II) bromide,
see: X. Qian, A. Auffrant, A. Felouat, C. Gosmini,
Angew. Chem. Int. Ed. 2011, 50, 10402 –10405; Angew.
Chem. 2011, 123, 10586-10589; b) P. Gomes, C.
Gosmini, J. Périchon, Org. Lett. 2003, 5, 1043-1047.
[13] A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2015,
55, 58-102; Angew. Chem. 2015, 128, 58-106.
[25] J.-F. Han, P. Guo, X.-G. Zhang, J.-B. Liao, K.-Y. Ye,
Org. Biom. Chem. 2020, DOI: 10.1039/d0ob01581d.
[14] C. K. Prier, D. A. Rankic, D. W. C. MacMillan,
[26] a) K. Takizawa, T. Sekino, S. Sato, T. Yoshino, M.
Kojima, S. Matsunaga, Angew. Chem., 2019, 131,
9297-9231; Angew. Chem. Int. Ed., 2019, 58, 9199 –
9203; (b) T. Sekino, S. Sato, K. Kuwabara, K.
Takizawa, T. Yoshino, M. Kojima, S. Matsunaga,
Synthesis, 2020, 52, 1934–1946.
Chem. Rev. 2013, 113, 5322-5363.
[15] J. A. Milligan, J. P. Phelan Shorouk, O. Badir, G. A.
Molander, Angew. Chem. Int. Ed. 2019, 58, 6152-6163;
Angew. Chem. 2019, 131, 6212-6224.
[16] J. Twilton, C. Lee, P. Zhang, M. H. Shaw, R. W.
Evans, D. W. C. MacMillan, Nature Rev. Chem. 2017,
1, 0052.
[27] M. Lombardo, A. Gualandi, F. Pasi, C. Trombini, Adv.
Synth. Catal. 2007, 349, 465-468, and ref. therein.
[17] a) L. Pitzer, J. L. Schwarz, F. Glorius, Chem. Sci.
2019, 10, 8285-8291; b) R. J., Wiles, G. A. Molander,
Isr. J. Chem. 2020, 60, 281-293.
[28] A. Call, C. Casadevall, F. Acũna-Parés, A. Casitas, J.
Lloret-Fillol, Chem. Commun. 2017, 8, 4739–4749.
[29] P. Gomes, O. Buriez, E. Labbé, C. Gosmini, J.
[18] a) J. L. Schwarz, F. Schäfers, A. Tlahuext-Aca, L.
Périchon, J. Electroanal. Chem. 2004, 562, 255–260.
Lückemeier, F. Glorius, J. Am. Chem. Soc. 2018, 140,
6
This article is protected by copyright. All rights reserved.