Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a Ni
aryl electrophiles
etherification
homogeneous catalysis
nickel
photocatalysis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
27 Jul 2020
27 Jul 2020
Historique:
received:
05
03
2020
revised:
06
04
2020
pubmed:
14
4
2020
medline:
14
4
2020
entrez:
14
4
2020
Statut:
ppublish
Résumé
A highly effective C-O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a Ni
Identifiants
pubmed: 32281220
doi: 10.1002/anie.202003359
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
12714-12719Subventions
Organisme : National Natural Science Foundation of China
ID : 21871171
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
S. Enthaler, A. Company, Chem. Soc. Rev. 2011, 40, 4912;
G. Evano, J. J. Wang, A. Nitelet, Org. Chem. Front. 2017, 4, 2480;
E. N. Pitsinos, V. P. Vidali, E. A. Couladouros, Eur. J. Org. Chem. 2011, 1207;
S. D. Roughley, A. M. Jordan, J. Med. Chem. 2011, 54, 3451.
E. Fuhrmann, J. Talbiersky, Org. Process Res. Dev. 2005, 9, 206.
K. C. K. Swamy, N. N. B. Kumar, E. Balaraman, K. V. P. Kumar, Chem. Rev. 2009, 109, 2551.
“Nucleophilic Aromatic Substitution”: S. Caron, A. Ghosh, Practical Synthetic Organic Chemistry, Wiley, Hoboken, 2011, pp. 237-253.
Reviews on the metal-catalyzed C−O cross-coupling:
K. Keerthi Krishnan, S. M. Ujwaldev, K. S. Sindhu, G. Anilkumar, Tetrahedron 2016, 72, 7393;
S. Bhunia, G. G. Pawar, S. V. Kumar, Y. W. Jiang, D. W. Ma, Angew. Chem. Int. Ed. 2017, 56, 16136;
Angew. Chem. 2017, 129, 16352.
Selected examples of Pd-catalyzed C−O cross-coupling:
K. E. Torraca, X. Huang, C. A. Parrish, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 10770;
A. V. Vorogushin, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 8146;
G. J. Withbroe, R. A. Singer, J. E. Sieser, Org. Process Res. Dev. 2008, 12, 480;
E. J. Milton, J. A. Fuentes, M. L. Clarke, Org. Biomol. Chem. 2009, 7, 2645;
S. Gowrisankar, A. G. Sergeev, P. Anbarasan, A. Spannenberg, H. Neumann, M. Beller, J. Am. Chem. Soc. 2010, 132, 11592;
X. Wu, B. P. Fors, S. L. Buchwald, Angew. Chem. Int. Ed. 2011, 50, 9943;
Angew. Chem. 2011, 123, 10117;
S. Gowrisankar, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 2498;
P. E. Maligres, J. Li, S. W. Krska, J. D. Schreier, I. T. Raheem, Angew. Chem. Int. Ed. 2012, 51, 9071;
Angew. Chem. 2012, 124, 9205;
C. W. Cheung, S. L. Buchwald, Org. Lett. 2013, 15, 3998;
T. M. Rangarajan, R. Singh, R. Brahma, K. Devi, R. P. Singh, A. K. Prasad, Chem. Eur. J. 2014, 20, 14218;
R. S. Sawatzky, B. K. V. Hargreaves, M. Stradiotto, Eur. J. Org. Chem. 2016, 2444;
H. Zhang, P. Ruiz-Castillo, S. L. Buchwald, Org. Lett. 2018, 20, 1580.
Selected examples of Cu-catalyzed C−O cross-coupling:
M. Wolter, G. Nordmann, G. E. Job, S. L. Buchwald, Org. Lett. 2002, 4, 973;
H. Zhang, D. W. Ma, W. Cao, Synlett 2007, 0243;
R. A. Altman, A. Shafir, A. Choi, P. A. Lichtor, S. L. Buchwald, J. Org. Chem. 2008, 73, 284;
J. Niu, H. Zhou, Z. Li, J. Xu, S. Hu, J. Org. Chem. 2008, 73, 7814;
A. B. Naidu, E. A. Jaseer, G. Sekar, J. Org. Chem. 2009, 74, 3675;
Z. Chen, Y. Jiang, L. Zhang, Y. Guo, D. Ma, J. Am. Chem. Soc. 2019, 141, 3541.
Ni-catalyzed C−O cross-coupling:
P. M. MacQueen, J. P. Tassone, C. Diaz, M. Stradiotto, J. Am. Chem. Soc. 2018, 140, 5023;
J. A. Terrett, J. D. Cuthbertson, V. W. Shurtleff, D. W. C. MacMillan, Nature 2015, 524, 330;
Q.-Q. Zhou, F.-D. Lu, D. Liu, L.-Q. Lu, W.-J. Xiao, Org. Chem. Front. 2018, 5, 3098.
Ni-catalyzed C−N coupling using soluble organic bases:
R. Y. Liu, J. M. Dennis, S. L. Buchwald, J. Am. Chem. Soc. 2020, ASAP, https://doi.org/10.1021/jacs.0c00286; Pd-catalyzed amination reactions using soluble organic bases:
L. M. Baumgartner, J. M. Dennis, N. A. White, S. L. Buchwald, K. F. Jensen, Org. Process Res. Dev. 2019, 23, 1594;
J. M. Dennis, N. A. White, R. Y. Liu, S. L. Buchwald, ACS Catal. 2019, 9, 3822;
J. M. Dennis, N. A. White, R. Y. Liu, S. L. Buchwald, J. Am. Chem. Soc. 2018, 140, 4721.
V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047.
S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299;
V. P. Ananikov, ACS Catal. 2015, 5, 1964.
L. Yang, Z. Huang, G. Li, W. Zhang, R. Cao, C. Wang, J. Xiao, D. Xue, Angew. Chem. Int. Ed. 2018, 57, 1968;
Angew. Chem. 2018, 130, 1986.
Selected examples of coupling reactions without the use of external photosensitizers:
S. E. Creutz, K. J. Lotito, G. C. Fu, J. C. Peters, Science 2012, 338, 647;
Q. M. Kainz, C. D. Matier, A. Bartoszewicz, S. L. Zultanski, J. Peters, G. C. Fu, Science 2016, 351, 681;
G.-Z. Wang, R. Shang, W.-M. Cheng, Y. Fu, J. Am. Chem. Soc. 2017, 139, 18307;
P. Chuentragool, D. Kurandina, V. Gevorgyan, Angew. Chem. Int. Ed. 2019, 58, 11586;
Angew. Chem. 2019, 131, 11710.
Recent studies on nickel(II)-aryl halide complexes:
B. J. Shields, B. Kudisch, G. D. Scholes, A. G. Doyle, J. Am. Chem. Soc. 2018, 140, 3035;
B. J. Shields, A. G. Doyle, J. Am. Chem. Soc. 2016, 138, 12719;
L. Tian, N. A. Till, B. Kudisch, D. W. C. MacMillan, G. D. Scholes, J. Am. Chem. Soc. 2020, 142, 4555;
S. I. Ting, S. Garakyaraghi, C. M. Taliaferro, B. J. Shields, G. D. Scholes, F. N. Castellano, A. G. Doyle, J. Am. Chem. Soc. 2020, 142, 5800.
For details, see the Supporting Information.
J. B. Sperry, K. E. P. Wiglesworth, I. Edmonds, P. Fiore, D. C. Boyles, D. B. Damon, R. L. Dorow, E. L. P. Chekler, J. Langille, J. W. Coe, Org. Process Res. Dev. 2014, 18, 1752.
Selected examples of Pd-catalyzed reactions:
S. Kuwabe, K. E. Torraca, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 12202;
K. E. O. Ylijoki, E. P. Kϋndig, Chem. Commun. 2011, 47, 10608;
L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu, G. Satyanarayana, Org. Lett. 2012, 14, 628;
W. Yang, J. Yan, Y. Long, S. Zhang, J. Liu, Y. Zeng, Q. Cai, Org. Lett. 2013, 15, 6022;
J. Shi, T. Wang, Y. Huang, X. Zhang, Y. Wu, Q. Cai, Org. Lett. 2015, 17, 840; Cu-catalyzed reactions:
J. Niu, P. Guo, J. Kang, Z. Li, J. Xu, S. Hu, J. Org. Chem. 2009, 74, 5075;
W. Yang, Y. Liu, S. Zhang, Q. Cai, Angew. Chem. Int. Ed. 2015, 54, 8805;
Angew. Chem. 2015, 127, 8929; Ni-catalyzed reactions:
S.-J. Han, R. Doi, B. M. Stoltz, Angew. Chem. Int. Ed. 2016, 55, 7437;
Angew. Chem. 2016, 128, 7563.
L. Fumagalli, M. Pallavicini, R. Budriesi, C. Bolchi, M. Canovi, A. Chiarini, G. Chiodini, M. Gobbi, P. Laurino, M. Micucci, V. Straniero, E. Valoti, J. Med. Chem. 2013, 56, 6402;
L. I. Pilkington, D. Barker, Nat. Prod. Rep. 2015, 32, 1369.
R. Sun, Y. Qin, S. Ruccolo, C. Schnedermann, C. Costentin, D. G. Nocera, J. Am. Chem. Soc. 2019, 141, 89;
R. Sun, Y. Qin, D. G. Nocera, Angew. Chem. Int. Ed. 2020, https://doi.org/10.1002/anie.201916398;
Angew. Chem. 2020, https://doi.org/10.1002/anie.201916398.
K. M. Arendt, A. G. Doyle, Angew. Chem. Int. Ed. 2015, 54, 9876;
Angew. Chem. 2015, 127, 10014.
In the 3MLCT state, nickel is formally NiIII, which could undergo reductive elimination to form the ester: P. Ma, S. Wang, H. Chen, ACS Catal. 2020, 10, 1.
DBU could also act an electron donor, reducing NiII to NiI under irradiation: C.-H. Lim, M. Kudisch, B. Liu, G. M. Miyake, J. Am. Chem. Soc. 2018, 140, 7667; Also see the Supporting Information on the redox potential of excited A (Figure S5) and DBU (Figure S6).
The NiI may interact with the NiII species, forming an inactive bimetallic complex; see Ref. [19a].
The off-cycle NiII species could not be clearly defined in terms of quantity and the identity of the anion, and its conversion to NiI is not clear either. Based on recent reports, it could be converted back into NiI through photo-induced disproportionation (Ref. [14a]), photo-induced radical dissociation (Ref. [14d]), or photo-induced reduction by DBU (Ref. [22]). In all cases there should be byproduct(s), which is not shown, however.