Visible Light-Promoted C–C Bond Formation from Hydroxyaryls in Water
Dafne Saporito A , Sergio A. Rodriguez B and Maria T. Baumgartner A C
+ Author Affiliations
- Author Affiliations
A INFIQC – Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
B CONICET, Instituto de Ciencias Químicas, Facultad de Agronomía y Agroindustrias, Universidad Nacional de Santiago del Estero, Av. Belgrano Sur 1912, Santiago del Estero 4200, Argentina.
C Corresponding author. Email: tere@fcq.unc.edu.ar
Australian Journal of Chemistry 72(12) 978-982 https://doi.org/10.1071/CH19378
Submitted: 5 August 2019 Accepted: 7 October 2019 Published: 8 November 2019
Abstract
An eco-friendly and direct arylation of hydroxyaryls in water using photoinduced reactions with different substrates (1-bromo-2-naphthol, 1-iodo-2-naphthol, N-(2-iodophenyl)acetamide, 5-bromouracil, 2-iodo-N-methylbenzamide, and 2-iodobenzamide) was studied. For example, π-expanded coumarins, compounds with potential optical applications, were synthesized in very high yield, without the use of toxic reagents, in a one-pot reaction. In addition, we demonstrate that the irradiation source (halogen lamp) can be efficiently replaced by an LED without altering the reaction yield.
References
[1] D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893.| Crossref | GoogleScholarGoogle Scholar | 12630855PubMed |
[2] (a) H. Li, A. Sasmal, X. Shi, J.-F. Soulé, H. Doucet, Org. Biomol. Chem. 2018, 16, 4399.
| Crossref | GoogleScholarGoogle Scholar | 29786741PubMed |
(b) T. Besson, C. Fruit, Synthesis 2016, 3879.
| Crossref | GoogleScholarGoogle Scholar |
(c) R. Rossi, M. Lessi, C. Manzinia, G. Marianetti, Synthesis 2016, 3821.
| Crossref | GoogleScholarGoogle Scholar |
(d) A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722.
| Crossref | GoogleScholarGoogle Scholar |
[3] (a) A. Albini, M. Fagnoni, Photochemically Generated Intermediates in Synthesis 2013 (John Wiley & Sons: Hoboken, NJ).
(b) D. Ravelli, S. Protti, M. Fagnoni, Chem. Rev. 2016, 116, 9850.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) M. F. Saraiva, M. R. C. Couri, M. Le Hyaric, M. V. de Almeida, Tetrahedron 2009, 65, 3563.
| Crossref | GoogleScholarGoogle Scholar |
(b) F. Minisci, E. Vismara, F. Fontana, M. C. A. Nogueira Barbosa, Tetrahedron Lett. 1989, 30, 4569.
| Crossref | GoogleScholarGoogle Scholar |
(c) L. Pretali, F. Doria, D. Verga, A. Profumo, M. Freccero, J. Org. Chem. 2009, 74, 1034.
| Crossref | GoogleScholarGoogle Scholar |
(d) S. Lazzaroni, D. Ravelli, S. Protti, M. Fagnoni, A. Albini, C. R. Chim. 2017, 20, 261.
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) N. Hoffmann, J. Phys. Org. Chem. 2015, 28, 121.
| Crossref | GoogleScholarGoogle Scholar |
(b) S. Protti, M. Fagnoni, D. Ravelli, ChemCatChem 2015, 7, 1516.
| Crossref | GoogleScholarGoogle Scholar |
(c) D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97.
| Crossref | GoogleScholarGoogle Scholar |
[6] (a) M. Schmittel, A. Burghart, Angew. Chem. Int. Ed. Engl. 1997, 36, 2550.
| Crossref | GoogleScholarGoogle Scholar |
(b) M. Mella, M. Fagnoni, M. Freccero, E. Fasani, A. Albini, Chem. Soc. Rev. 1998, 27, 81.
| Crossref | GoogleScholarGoogle Scholar |
(c) N. Hoffmann, J. Photochem. Photobiol. Chem. 2008, 9, 43.
| Crossref | GoogleScholarGoogle Scholar |
(d) M. A. Ischay, T. P. Yoon, Eur. J. Org. Chem. 2012, 3359.
| Crossref | GoogleScholarGoogle Scholar |
[7] R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 2003, 103, 71.
| Crossref | GoogleScholarGoogle Scholar | 12517182PubMed |
[8] A. B. Peñéñory, J. E. Arguello, in Handbook of Synthetic Photochemistry (Eds A. Albini, M. Fagnoni) 2010, Ch. 10, pp. 319–346 (Wiley-VCH: Weinheim).
[9] (a) R. A. Rossi, M. T. Baumgartner, in Targets in Heterocyclic Systems: Chemistry and Properties (Eds O. A. Attanasi, D. Spinelli) 1999, Vol. 3, pp. 215–243 (Societa Chimica Italiana: Camerino).
(b) J. I. Bardagí, M. E. Budén, R. A. Rossi, in Targets in Heterocyclic Systems: Chemistry and Properties (Eds O. A. Attanasi, D. Spinelli, P. Merino) 2016, Vol. 20, pp. 247–282 (Societa Chimica Italiana: Rome).
[10] W. Guerra, R. A. Rossi, A. B. Pierini, S. M. Barolo, J. Org. Chem. 2016, 81, 4965.
| Crossref | GoogleScholarGoogle Scholar | 27166973PubMed |
[11] W. Guerra, R. A. Rossi, A. B. Pierini, S. M. Barolo, J. Org. Chem. 2015, 80, 928.
| Crossref | GoogleScholarGoogle Scholar | 25490433PubMed |
[12] M. E. Buden, V. B. Dorn, M. Gamba, A. B. Pierini, R. A. Rossi, J. Org. Chem. 2010, 75, 2206.
| Crossref | GoogleScholarGoogle Scholar | 20210329PubMed |
[13] J. K. Laha, S. M. Barolo, R. A. Rossi, G. D. Cuny, J. Org. Chem. 2011, 76, 6421.
| Crossref | GoogleScholarGoogle Scholar | 21739958PubMed |
[14] (a) P. Camargo Solórzano, F. Brigante, A. B. Pierini, L. B. Jimenez, J. Org. Chem. 2018, 83, 7867.
| Crossref | GoogleScholarGoogle Scholar | 29856222PubMed |
(b) T. C. Tempesti, A. B. Pierini, M. T. Baumgartner, J. Org. Chem. 2005, 70, 6508.
| Crossref | GoogleScholarGoogle Scholar |
[15] M. E. Buden, J. I. Bardagí, M. Puiatti, R. A. Rossi, J. Org. Chem. 2017, 82, 8325.
| Crossref | GoogleScholarGoogle Scholar | 28553981PubMed |
[16] M. T. Baumgartner, T. C. Tempesti, A. B. Pierini, Arkivoc 2003, 420.
| Crossref | GoogleScholarGoogle Scholar |
[17] 4 does not decompose with base, light or at 50°C.
[18] (a) The ortho aryl acetanilides are important synthetic intermediates: J. Hubrich, T. Himmler, L. Rodefeld, L. Ackermann, Adv. Synth. Catal. 2015, 357, 474.
| Crossref | GoogleScholarGoogle Scholar |
(b) P. Natarajan, P. Ya, D. Chuskit, Green Chem. 2017, 19, 5854.
| Crossref | GoogleScholarGoogle Scholar |
[19] J. I. Bardagi, I. Ghosh, M. Schmalzbauer, T. Ghosh, B. König, Eur. J. Org. Chem. 2018, 34.
| Crossref | GoogleScholarGoogle Scholar |
[20] 6 : 1 ratio = 1 : 5. [6] = 101 mM; [base]= 516 mM.
[21] W. Xu, K. M. Chan, E. T. Kool, Nat. Chem. 2017, 9, 1043.
| Crossref | GoogleScholarGoogle Scholar | 29064490PubMed |
[22] S. A. Rodríguez, M. T. Baumgartner, Tetrahedron Lett. 2010, 51, 5322.
| Crossref | GoogleScholarGoogle Scholar |
[23] S. E. Braslavsky, Pure Appl. Chem. 2007, 79, 293.
| Crossref | GoogleScholarGoogle Scholar |
[24] M. T. Baumgartner, M. H. Gallego, A. B. Pierini, J. Org. Chem. 1998, 63, 6394.
| Crossref | GoogleScholarGoogle Scholar | 11672276PubMed |
[25] Y. Chiang, A. J. Kresge, Y. S. Tang, J. Wirz, J. Am. Chem. Soc. 1984, 106, 460.
| Crossref | GoogleScholarGoogle Scholar |
[26] J. W. Bunting, J. P. Kanter, R. Nelander, Z. Wu, Can. J. Chem. 1995, 73, 1305.
| Crossref | GoogleScholarGoogle Scholar |
[27] T. C. Tempesti, A. B. Pierini, M. T. Baumgartner, New J. Chem. 2009, 33, 1523.
| Crossref | GoogleScholarGoogle Scholar |
[28] M. T. Baumgartner, M. A. Nazareno, M. C. Murguía, A. B. Pierini, R. A. Rossi, Synthesis 1999, 2053.
| Crossref | GoogleScholarGoogle Scholar |
[29] M. Tasior, D. Kim, S. Singha, M. Krzeszewski, K. H. Ahn, D. T. J. Gryko, J. Mater. Chem. C 2015, 3, 1421.
| Crossref | GoogleScholarGoogle Scholar |
[30] (a) B. Pfundstein, S. K. El Desouky, W. E. Hull, R. Haubner, G. Erben, R. W. Owen, Phytochemistry 2010, 71, 1132.
| Crossref | GoogleScholarGoogle Scholar | 20451939PubMed |
(b) Y. Gaoni, R. Mechoulam, J. Am. Chem. Soc. 1964, 86, 1646.
| Crossref | GoogleScholarGoogle Scholar |
(c) G. Bringmann, D. Menche, Acc. Chem. Res. 2001, 34, 615.
| Crossref | GoogleScholarGoogle Scholar |
(d) G. Bringmann, T. Gulder, T. A. M. Gulder, in Asymmetric Synthesis – The Essentials, 2nd edn (Eds S. Bräse, M. Christmann) 2008, pp. 260–264 (Wiley-VCH: Weinheim).
[31] (a) D. V. Kadnikov, R. C. Larock, J. Org. Chem. 2003, 68, 9423.
| Crossref | GoogleScholarGoogle Scholar | 14629168PubMed |
(b) C. Jia, D. Piao, T. Kitamura, Y. Fujiwara, J. Org. Chem. 2000, 65, 7516.
| Crossref | GoogleScholarGoogle Scholar |
(c) Y. Luo, J. Wu, Tetrahedron Lett. 2009, 50, 2103.
| Crossref | GoogleScholarGoogle Scholar |
(d) L. Zhang, T. Meng, R. Fan, J. Wu, J. Org. Chem. 2007, 72, 7279.
| Crossref | GoogleScholarGoogle Scholar |
(e) Q. Zhu, J. Wu, R. Fathi, Z. Yang, Org. Lett. 2002, 4, 3333.
| Crossref | GoogleScholarGoogle Scholar |
[32] Y. Li, Y.-J. Ding, J.-Y. Wang, Y.-M. Su, X.-S. Wang, Org. Lett. 2013, 15, 2574.
| Crossref | GoogleScholarGoogle Scholar | 23662848PubMed |
