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Synlett 2025; 36(02): 137-140
DOI: 10.1055/a-2301-2854
DOI: 10.1055/a-2301-2854
letter
Phenylazo-BODIPYs: Direct Access via Pd-Catalysis
This work was funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation, WE2932/14-1) and livMatS Cluster of Excellence under Germany’s Excellence Strategy (EXC-2193/1-390951807).
Abstract
A new type of functionalized BODIPY dyes is described. Utilizing an established procedure for Buchwald–Hartwig reactions, we have been able to convert α-chloro BODIPYs to α-azo-BODIPYs using phenylhydrazines. Optimization of the reaction conditions and variation of the BODIPY core and the phenylhydrazine were conducted. Absorption and emission spectra were recorded.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2301-2854.
- Supporting Information
Publication History
Received: 09 March 2024
Accepted after revision: 06 April 2024
Accepted Manuscript online:
06 April 2024
Article published online:
30 April 2024
© 2024. Thieme. All rights reserved
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References and Notes
- 1 Treibs A, Kreuzer F.-H. Justus Liebigs Ann. Chem. 1968; 718: 208
- 2a Loudet A, Burgess K. Chem. Rev. 2007; 107: 4891
- 2b Ulrich G, Ziessel R, Harriman A. Angew. Chem. Int. Ed. 2008; 47: 1184
- 2c Lakshmi V, Rao MR, Ravikanth M. Org. Biomol. Chem. 2015; 13: 2501
- 2d Boens N, Verbelen B, Ortiz MJ, Jiao L, Dehaen W. Coord. Chem. Rev. 2019; 399: 213024
- 2e Liu Z, Jiang Z, Yan M, Wang X. Front. Chem. 2019; 7: 712
- 2f Gapare RL, Thompson A. Chem. Commun. 2022; 58: 7351
- 3a Rao MR, Mobin SM, Ravikanth M. Tetrahedron 2010; 66: 1728
- 3b Wu W, Guo H, Wu W, Ji S, Zhao J. J. Org. Chem. 2011; 76: 7056
- 3c Drivas TG, Bennett J. Neuron 2012; 75: 185
- 3d Polosukhina A, Litt J, Tochitsky I, Nemargut J, Sychev Y, de Kouchkovsky I, Huang T, Borges K, Trauner D, van Gelder RN, Kramer RH. Neuron 2012; 75: 271
- 3e Er JC, Leong C, Teoh CL, Yuan Q, Merchant P, Dunn M, Sulzer D, Sames D, Bhinge A, Kim D, Kim S.-M, Yoon M.-H, Stanton LW, Je SH, Yun S.-W, Chang Y.-T. Angew. Chem. Int. Ed. 2015; 54: 2442
- 3f Patalag LJ, Ulrichs JA, Jones PG, Werz DB. Org. Lett. 2017; 19: 2090
- 3g Franke JM, Raliski BK, Boggess SC, Natesan DV, Koretsky ET, Zhang P, Kulkarni RU, Deal PE, Miller EW. J. Am. Chem. Soc. 2019; 141: 12824
- 3h Gomez AM, Lopez JC. Pure Appl. Chem. 2019; 91: 1073
- 3i Porubský M, Gurská S, Stanková J, Hajdúch M, Džubák P, Hlaváč J. RSC Adv. 2019; 9: 25075
- 3j Patalag LJ, Ahadi S, Lashchuk O, Jones PG, Ebbinghaus S, Werz DB. Angew. Chem. Int. Ed. 2021; 60: 8766
- 3k Patalag LJ, Hoche J, Holzapfel M, Schmiedel A, Mitric R, Lambert C, Werz DB. J. Am. Chem. Soc. 2021; 143: 7414
- 3l Blázquez-Moraleja A, Maierhofer L, Mann E, Prieto-Montero R, Oliden-Sánchez A, Celada L, Martínez-Martínez V, Chiara M.-D, Chiara JL. Org. Chem. Front. 2022; 9: 5774
- 3m Koczorowski T, Glowacka-Sobotta A, Sysak S, Mlynarczyk DT, Lesyk R, Goslinski T, Sobotta L. Appl. Sci. 2022; 12: 7815
- 3n Selvaggio G, Nißler R, Nietmann P, Patra A, Patalag LJ, Janshoff A, Werz DB, Kruss S. Analyst 2022; 147: 230
- 3o Bozzi ÍA. O, Machado LA, Diogo EB. T, Delolo FG, Barros LO. F, Graça GA. P, Araujo MH, Martins FT, Pedrosa LF, da Luz LC, Moraes ES, Rodembusch FS. J. S. F, Oliveira AG, Röttger SH, Werz DB, Souza CP, Fantuzzi F, Han J, Marder TB, Braunschweig H, da Silva EN. Jr. Chem. Eur. J. 2023; 30: e202303883
- 3p Socrier L, Sharma A, Chen T, Flato K, Kettelhoit K, Enderlein J, Werz DB, Steinem C. Biophys. J. 2023; 122: 4104
- 3q Gong Q, Wu Q, Guo X, Li W, Wang L, Hao E, Jiao L. Org. Lett. 2021; 23: 7220
- 5a Feringa BL, van Delden RA, Koumura N, Geertsema EM. Chem. Rev. 2000; 100: 1789
- 5b Norikane Y, Tamaoki N. Org. Lett. 2004; 6: 2595
- 5c Tochitsky I, Helft Z, Meseguer V, Fletcher RB, Vessey KA, Telias M, Denlinger B, Malis J, Fletcher EL, Kramer RH. Neuron 2016; 92: 100
- 5d Crespi S, Simeth NA, König B. Nat. Rev. Chem. 2019; 3: 133
- 5e Alsantali RI, Raja QA, Alzahrani AY, Sadiq A, Naeem N, Mughal EU, Al-Rooqi MM, El Guesmi N, Moussa Z, Ahmed SA. Dyes Pigm. 2022; 199: 110050
- 5f Mezgebe K, Mulugeta E. RSC Adv. 2022; 12: 25932
- 5g Griwatz JH, Campi CE, Kunz A, Wegner HA. ChemSusChem 2024; e202301714
- 5h Sun C.-L, Wang C, Boulatov R. ChemPhotoChem 2019; 3: 268
- 5i Velema WA, Szymanski W, Feringa BL. J. Am. Chem. Soc. 2014; 136: 2178
- 5j Morstein J, Romano G, Hetzler BE, Plante A, Haake C, Levitz J, Trauner D. Angew. Chem. Int. Ed. 2022; 61: e202117094
- 6 Merino E. Chem. Soc. Rev. 2011; 40: 3835
- 7 Yokoi H, Hiroto S, Shinokubo H. Org. Lett. 2014; 16: 3004
- 8 Wen B, Li C, Kang B, Zheng T, Wang Y, Jiang Y, Xu L, Oh J, Osuka A, Kim D. Chem. Eur. J. 2023; 30: e202303193
- 9 Rao Y, Xu L, Zhou M, Yin B, Osuka A, Song J. Angew. Chem. Int. Ed. 2022; 134: e202206899
- 10 von Köller HF, Geffers FJ, Kalvani P, Foraita A, Loß P.-EJ, Butschke B, Jones PG, Werz DB. Chem. Commun. 2023; 59: 14697
- 11 Lundgren RJ, Stradiotto M. Angew. Chem. Int. Ed. 2010; 49: 8686
- 12 DeAngelis A, Wang D.-H, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 3434
- 13 Luna-Mora RA, Torres-Reyes Á, González-Cruz OA, Ortega-Jiménez F, Ríos-Guerra H, González-Carrillo JV, Barrera-Téllez F, Perez-Flores J, Penieres-Carrillo JG. Green Chem. Lett. Rev. 2018; 11: 371
- 14 Guisán-Ceinos SR, Rivero A, Romeo-Gella F, Simón-Fuente S, Gómez-Pastor S, Calvo N, Orrego AH, Guisán JM, Corral I, Sanz-Rodriguez F, Ribagorda M. J. Am. Chem. Soc. 2022; 144: 8185
- 15a Chen L, Li F, Li Y, Yang J, Li Y, He B. Chem. Commun. 2021; 58: 298
- 15b Röttger SH, Patalag LJ, Hasenmaile F, Milbrandt L, Butschke B, Jones PG, Werz DB. Org. Lett. 2024; 26: 3020
- 16 Dilek Ö, Bane SL. Tetrahedron Lett. 2008; 49: 1413
- 17 Vetráková Ľ, Ladányi V, Al Anshori J, Dvořák P, Wirz J, Heger D. Photochem. Photobiol. Sci. 2017; 16: 1749
- 18 Leen V, Leemans T, Boens N, Dehaen W. Eur. J. Org. Chem. 2011; 4386
- 19 Klessinger M. Chem. Unserer Zeit 1978; 12: 1
- 20 Heijkoop G, van Beek HC. A. Recl. Trav. Chim. Pays-Bas 1976; 95: 6
- 21 Dorel R, Grugel CP, Haydl AM. Angew. Chem. Int. Ed. 2019; 58: 17118
- 22 General Procedure for the Synthesis of Phenylazo-BODIPYs An α-chloro BODIPY (1.0 equiv) and a phenylhydrazine or its hydrochloride (1.5 equiv) together with Pd(OAc)2 (10 mol%), (±)-BINAP (15 mol%) and Cs2CO3 (1.5-3.0 equiv) were dissolved in anhydrous PhMe (0.0125 M with respect to the BODIPY) in a round-bottomed flask equipped with a magnetic stirring bar. The mixture was heated to 110 °C and stirred until the starting material was completely consumed and/or major product formation was observed. The solvent was removed under reduced pressure for subsequent purification.