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Angewandte Chemie - International Edition

Volumn 54, Issue 15, 2015, Pages 4612-4616

Radical C-H Arylation of the BODIPY Core with Aryldiazonium Salts: Synthesis of Highly Fluorescent Red-Shifted Dyes

(5) Verbelen, Bram a Boodts, Stijn a Hofkens, Johan a Boens, Noël a Dehaen, Wim a

a UNIVERSITY OF LEUVEN (Belgium)

Author keywords

arylation; BODIPY; dyes; photophysics; radicals

Indexed keywords

CHEMICAL REACTIONS; DYES; FLUORESCENCE; ORGANOMETALLICS; SALTS; SUBSTITUTION REACTIONS;

ARYL SUBSTITUENTS; ARYLATIONS; ARYLDIAZONIUM SALTS; BODIPY; PHOTOPHYSICS; RADICAL SPECIES; RADICALS; SYNTHETIC PROCEDURES;

AROMATIC COMPOUNDS;

EID: 85027935052 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201410853 Document Type: Article

Times cited : (121)

References (51)

1
- 84982338521
- A. Treibs, F.-H. Kreuzer, Liebigs Ann. Chem. 1968, 718, 208-223.
- (1968) Liebigs Ann. Chem. , vol.718 , pp. 208-223
- Treibs, A.¹ Kreuzer, F.-H.²

2
- 85028129434
- note
- The trade name BODIPY (acronym of boron dipyrrin or boron dipyrromethene), has become the common name for this class of fluorophores.

3
- 36849053388
- A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932
- (2007) Chem. Rev. , vol.107 , pp. 4891-4932
- Loudet, A.¹ Burgess, K.²

4
- 40849107127
- G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. 2008, 47, 1184-1201
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1184-1201
- Ulrich, G.¹ Ziessel, R.² Harriman, A.³

5
- 53749108591
- Angew. Chem. 2008, 120, 1202-1219.
- (2008) Angew. Chem. , vol.120 , pp. 1202-1219

6
- 79955522955
- M. Benstead, G. H. Mehl, R. W. Boyle, Tetrahedron 2011, 67, 3573-3601
- (2011) Tetrahedron , vol.67 , pp. 3573-3601
- Benstead, M.¹ Mehl, G.H.² Boyle, R.W.³

7
- 80054104219
- and references therein
- N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172, and references therein
- (2012) Chem. Soc. Rev. , vol.41 , pp. 1130-1172
- Boens, N.¹ Leen, V.² Dehaen, W.³

8
- 84868124530
- S. G. Awuah, Y. You, RSC Adv. 2012, 2, 11169-11183
- (2012) RSC Adv. , vol.2 , pp. 11169-11183
- Awuah, S.G.¹ You, Y.²

9
- 84870533561
- A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung, K. Burgess, Chem. Soc. Rev. 2013, 42, 77-88
- (2013) Chem. Soc. Rev. , vol.42 , pp. 77-88
- Kamkaew, A.¹ Lim, S.H.² Lee, H.B.³ Kiew, L.V.⁴ Chung, L.Y.⁵ Burgess, K.⁶

10
- 84899074233
- A. Bessette, G. S. Hanan, Chem. Soc. Rev. 2014, 43, 3342-3405
- (2014) Chem. Soc. Rev. , vol.43 , pp. 3342-3405
- Bessette, A.¹ Hanan, G.S.²

11
- 84904731459
- S. P. Singh, T. Gayathri, Eur. J. Org. Chem. 2014, 4689-4707.
- (2014) Eur. J. Org. Chem. , pp. 4689-4707
- Singh, S.P.¹ Gayathri, T.²

12
- 0032740860
- A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenspies, K. Burgess, J. Org. Chem. 1999, 64, 7813-7819
- (1999) J. Org. Chem. , vol.64 , pp. 7813-7819
- Burghart, A.¹ Kim, H.² Welch, M.B.³ Thoresen, L.H.⁴ Reibenspies, J.⁵ Burgess, K.⁶

13
- 13844253910
- A. B. Zaitsev, R. Méallet-Renault, E. Y. Schmidt, A. I. Mikhaleva, S. Badré, C. Dumas, A. M. Vasil'tsov, N. V. Zorina, R. B. Pansu, Tetrahedron 2005, 61, 2683-2688
- (2005) Tetrahedron , vol.61 , pp. 2683-2688
- Zaitsev, A.B.¹ Méallet-Renault, R.² Schmidt, E.Y.³ Mikhaleva, A.I.⁴ Badré, S.⁵ Dumas, C.⁶ Vasil'tsov, A.M.⁷ Zorina, N.V.⁸ Pansu, R.B.⁹

14
- 79956062139
- L. N. Sobenina, A. M. Vasil'tsov, O. V. Petrova, K. B. Petrushenko, I. A. Ushakov, G. Clavier, R. Meallet-Renault, A. I. Mikhaleva, B. A. Trofimov, Org. Lett. 2011, 13, 2524-2527.
- (2011) Org. Lett. , vol.13 , pp. 2524-2527
- Sobenina, L.N.¹ Vasil'tsov, A.M.² Petrova, O.V.³ Petrushenko, K.B.⁴ Ushakov, I.A.⁵ Clavier, G.⁶ Meallet-Renault, R.⁷ Mikhaleva, A.I.⁸ Trofimov, B.A.⁹

15
- 26644452991
- M. Baruah, W. Qin, R. A. L. Vallée, D. Beljonne, T. Rohand, W. Dehaen, N. Boens, Org. Lett. 2005, 7, 4377-4380
- (2005) Org. Lett. , vol.7 , pp. 4377-4380
- Baruah, M.¹ Qin, W.² Vallée, R.A.L.³ Beljonne, D.⁴ Rohand, T.⁵ Dehaen, W.⁶ Boens, N.⁷

16
- 33644698915
- T. Rohand, M. Baruah, W. Qin, N. Boens, W. Dehaen, Chem. Commun. 2006, 266-268
- (2006) Chem. Commun. , pp. 266-268
- Rohand, T.¹ Baruah, M.² Qin, W.³ Boens, N.⁴ Dehaen, W.⁵

17
- 33750392902
- T. Rohand, W. Qin, N. Boens, W. Dehaen, Eur. J. Org. Chem. 2006, 4658-4663
- (2006) Eur. J. Org. Chem. , pp. 4658-4663
- Rohand, T.¹ Qin, W.² Boens, N.³ Dehaen, W.⁴

18
- 68149175208
- V. Leen, E. Braeken, K. Luckermans, C. Jackers, M. Van der Auweraer, N. Boens, W. Dehaen, Chem. Commun. 2009, 4515-4517
- (2009) Chem. Commun. , pp. 4515-4517
- Leen, V.¹ Braeken, E.² Luckermans, K.³ Jackers, C.⁴ Van Der Auweraer, M.⁵ Boens, N.⁶ Dehaen, W.⁷

19
- 70049094280
- L. Jiao, J. Li, S. Zhang, C. Wei, E. Hao, M. G. H. Vicente, New J. Chem. 2009, 33, 1888-1893
- (2009) New J. Chem. , vol.33 , pp. 1888-1893
- Jiao, L.¹ Li, J.² Zhang, S.³ Wei, C.⁴ Hao, E.⁵ Vicente, M.G.H.⁶

20
- 77950819907
- T. K. Khan, M. R. Rao, M. Ravikanth, Eur. J. Org. Chem. 2010, 2314-2323
- (2010) Eur. J. Org. Chem. , pp. 2314-2323
- Khan, T.K.¹ Rao, M.R.² Ravikanth, M.³

21
- 80054107166
- V. Leen, D. Miscoria, S. Yin, A. Filarowski, J. M. Ngongo, M. Van der Auweraer, N. Boens, W. Dehaen, J. Org. Chem. 2011, 76, 8168-8176
- (2011) J. Org. Chem. , vol.76 , pp. 8168-8176
- Leen, V.¹ Miscoria, D.² Yin, S.³ Filarowski, A.⁴ Ngongo, J.M.⁵ Van Der Auweraer, M.⁶ Boens, N.⁷ Dehaen, W.⁸

22
- 79961139992
- V. Leen, T. Leemans, N. Boens, W. Dehaen, Eur. J. Org. Chem. 2011, 4386-4396
- (2011) Eur. J. Org. Chem. , pp. 4386-4396
- Leen, V.¹ Leemans, T.² Boens, N.³ Dehaen, W.⁴

23
- 79958778415
- Y. Hayashi, S. Yamaguchi, W. Y. Cha, D. Kim, H. Shinokubo, Org. Lett. 2011, 13, 2992-2995
- (2011) Org. Lett. , vol.13 , pp. 2992-2995
- Hayashi, Y.¹ Yamaguchi, S.² Cha, W.Y.³ Kim, D.⁴ Shinokubo, H.⁵

24
- 84861793593
- G. Ulrich, A. Haefele, P. Retailleau, R. Ziessel, J. Org. Chem. 2012, 77, 5036-5048
- (2012) J. Org. Chem. , vol.77 , pp. 5036-5048
- Ulrich, G.¹ Haefele, A.² Retailleau, P.³ Ziessel, R.⁴

25
- 84871548948
- V. Leen, P. Yuan, L. Wang, N. Boens, W. Dehaen, Org. Lett. 2012, 14, 6150-6153.
- (2012) Org. Lett. , vol.14 , pp. 6150-6153
- Leen, V.¹ Yuan, P.² Wang, L.³ Boens, N.⁴ Dehaen, W.⁵

26
- 33646099627
- T. V. Goud, A. Tutar, J.-F. Biellmann, Tetrahedron 2006, 62, 5084-5091
- (2006) Tetrahedron , vol.62 , pp. 5084-5091
- Goud, T.V.¹ Tutar, A.² Biellmann, J.-F.³

27
- 35048850831
- E. Peña-Cabrera, A. Aguilar-Aguilar, M. González-Domínguez, E. Lager, R. Zamudio-Vázquez, J. Godoy-Vargas, F. Villanueva-García, Org. Lett. 2007, 9, 3985-3988
- (2007) Org. Lett. , vol.9 , pp. 3985-3988
- Peña-Cabrera, E.¹ Aguilar-Aguilar, A.² González-Domínguez, M.³ Lager, E.⁴ Zamudio-Vázquez, R.⁵ Godoy-Vargas, J.⁶ Villanueva-García, F.⁷

28
- 57549087050
- J. Han, O. Gonzalez, A. Aguilar-Aguilar, E. Peña-Cabrera, K. Burgess, Org. Biomol. Chem. 2009, 7, 34-36
- (2009) Org. Biomol. Chem. , vol.7 , pp. 34-36
- Han, J.¹ Gonzalez, O.² Aguilar-Aguilar, A.³ Peña-Cabrera, E.⁴ Burgess, K.⁵

29
- 80051786998
- I. J. Arroyo, R. Hu, B. Z. Tang, F. I. López, E. Peña-Cabrera, Tetrahedron 2011, 67, 7244-7250
- (2011) Tetrahedron , vol.67 , pp. 7244-7250
- Arroyo, I.J.¹ Hu, R.² Tang, B.Z.³ López, F.I.⁴ Peña-Cabrera, E.⁵

30
- 77954609582
- C. F. A. Gómez-Durán, I. García-Moreno, A. Costela, V. Martin, R. Sastre, J. Bañuelos, F. López Arbeloa, I. López Arbeloa, E. Peña-Cabrera, Chem. Commun. 2010, 46, 5103-5105
- (2010) Chem. Commun. , vol.46 , pp. 5103-5105
- Gómez-Durán, C.F.A.¹ García-Moreno, I.² Costela, A.³ Martin, V.⁴ Sastre, R.⁵ Bañuelos, J.⁶ López Arbeloa, F.⁷ López Arbeloa, I.⁸ Peña-Cabrera, E.⁹

31
- 84879379620
- J. O. Flores-Rizo, I. Esnal, C. A. Osorio-Martínez, C. F. A. Gómez-Durán, J. Bañuelos, I. López Arbeloa, K. H. Pannell, A. J. Metta-Magaña, E. Peña-Cabrera, J. Org. Chem. 2013, 78, 5867-5877.
- (2013) J. Org. Chem. , vol.78 , pp. 5867-5877
- Flores-Rizo, J.O.¹ Esnal, I.² Osorio-Martínez, C.A.³ Gómez-Durán, C.F.A.⁴ Bañuelos, J.⁵ López Arbeloa, I.⁶ Pannell, K.H.⁷ Metta-Magaña, A.J.⁸ Peña-Cabrera, E.⁹

32
- 72449170089
- L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792-9826
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9792-9826
- Ackermann, L.¹ Vicente, R.² Kapdi, A.R.³

33
- 77949410036
- Angew. Chem. 2009, 121, 9976-10011.
- (2009) Angew. Chem. , vol.121 , pp. 9976-10011

34
- 77049099859
- A. Wetzel, G. Pratsch, R. Kolb, M. R. Heinrich, Chem. Eur. J. 2010, 16, 2547-2556
- (2010) Chem. Eur. J. , vol.16 , pp. 2547-2556
- Wetzel, A.¹ Pratsch, G.² Kolb, R.³ Heinrich, M.R.⁴

35
- 84891781420
- A. Honraedt, M.-A. Raux, E. Le Grognec, D. Jacquemin, F.-X. Felpin, Chem. Commun. 2014, 50, 5236-5238.
- (2014) Chem. Commun. , vol.50 , pp. 5236-5238
- Honraedt, A.¹ Raux, M.-A.² Le Grognec, E.³ Jacquemin, D.⁴ Felpin, F.-X.⁵

36
- 34250642352
- C. Thivierge, R. Bandichhor, K. Burgess, Org. Lett. 2007, 9, 2135-2138
- (2007) Org. Lett. , vol.9 , pp. 2135-2138
- Thivierge, C.¹ Bandichhor, R.² Burgess, K.³

37
- 66349103604
- J. Chen, M. Mizumura, H. Shinokubo, A. Osuka, Chem. Eur. J. 2009, 15, 5942-5949
- (2009) Chem. Eur. J. , vol.15 , pp. 5942-5949
- Chen, J.¹ Mizumura, M.² Shinokubo, H.³ Osuka, A.⁴

38
- 77954049129
- V. Leen, V. Z. Gonzalvo, W. M. De Borggraeve, N. Boens, W. Dehaen, Chem. Commun. 2010, 46, 4908-4910
- (2010) Chem. Commun. , vol.46 , pp. 4908-4910
- Leen, V.¹ Gonzalvo, V.Z.² De Borggraeve, W.M.³ Boens, N.⁴ Dehaen, W.⁵

39
- 79952577448
- V. Leen, M. Van der Auweraer, N. Boens, W. Dehaen, Org. Lett. 2011, 13, 1470-1473.
- (2011) Org. Lett. , vol.13 , pp. 1470-1473
- Leen, V.¹ Van Der Auweraer, M.² Boens, N.³ Dehaen, W.⁴

40
- 84865220439
- B. Verbelen, V. Leen, L. Wang, N. Boens, W. Dehaen, Chem. Commun. 2012, 48, 9129-9131
- (2012) Chem. Commun. , vol.48 , pp. 9129-9131
- Verbelen, B.¹ Leen, V.² Wang, L.³ Boens, N.⁴ Dehaen, W.⁵

41
- 84876936771
- L. Wang, B. Verbelen, C. Tonnelé, D. Beljonne, R. Lazzaroni, V. Leen, W. Dehaen, N. Boens, Photochem. Photobiol. Sci. 2013, 12, 835-847.
- (2013) Photochem. Photobiol. Sci. , vol.12 , pp. 835-847
- Wang, L.¹ Verbelen, B.² Tonnelé, C.³ Beljonne, D.⁴ Lazzaroni, R.⁵ Leen, V.⁶ Dehaen, W.⁷ Boens, N.⁸

42
- 0043172126
- F. Minisci, E. Vismara, F. Fontana, G. Morini, M. Serravalle, C. Giordano, J. Org. Chem. 1986, 51, 4411-4416.
- (1986) J. Org. Chem. , vol.51 , pp. 4411-4416
- Minisci, F.¹ Vismara, E.² Fontana, F.³ Morini, G.⁴ Serravalle, M.⁵ Giordano, C.⁶

43
- 84941102542
- N. Santschi, J. Cvengroš, C. Matthey, E. Otth, A. Togni, Eur. J. Org. Chem. 2014, 6371-6375.
- (2014) Eur. J. Org. Chem. , pp. 6371-6375
- Santschi, N.¹ Cvengroš, J.² Matthey, C.³ Otth, E.⁴ Togni, A.⁵

44
- 2942545129
- C. Galli, Chem. Rev. 1988, 88, 765-792.
- (1988) Chem. Rev. , vol.88 , pp. 765-792
- Galli, C.¹

45
- 33947470700
- J. K. Kochi, J. Am. Chem. Soc. 1957, 79, 2942-2948.
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 2942-2948
- Kochi, J.K.¹

46
- 0000986187
- A. L. J. Beckwith, R. J. Leydon, Tetrahedron Lett. 1963, 4, 385-388.
- (1963) Tetrahedron Lett. , vol.4 , pp. 385-388
- Beckwith, A.L.J.¹ Leydon, R.J.²

47
- 79958810405
- J. Bañuelos, V. Martín, C. F. A. Gómez-Durán, I. J. A. Córdoba, E. Peña-Cabrera, I. García-Moreno, A. Costela, M. E. Pérez-Ojeda, T. Arbeloa, I. L. Arbeloa, Chem. Eur. J. 2011, 17, 7261-7270
- (2011) Chem. Eur. J. , vol.17 , pp. 7261-7270
- Bañuelos, J.¹ Martín, V.² Gómez-Durán, C.F.A.³ Córdoba, I.J.A.⁴ Peña-Cabrera, E.⁵ García-Moreno, I.⁶ Costela, A.⁷ Pérez-Ojeda, M.E.⁸ Arbeloa, T.⁹ Arbeloa, I.L.¹⁰

48
- 84887021403
- I. Esnal, A. Urías-Benavides, C. F. A. Gómez-Durán, C. A. Osorio-Martínez, I. García-Moreno, A. Costela, J. Bañuelos, N. Epelde, I. López Arbeloa, R. Hu, B. Zhong Tang, E. Peña-Cabrera, Chem. Asian J. 2013, 8, 2691-2700
- (2013) Chem. Asian J. , vol.8 , pp. 2691-2700
- Esnal, I.¹ Urías-Benavides, A.² Gómez-Durán, C.F.A.³ Osorio-Martínez, C.A.⁴ García-Moreno, I.⁵ Costela, A.⁶ Bañuelos, J.⁷ Epelde, N.⁸ López Arbeloa, I.⁹ Hu, R.¹⁰ Zhong Tang, B.¹¹ Peña-Cabrera, E.¹²

49
- 84877146422
- R. I. Roacho, A. Metta-Magaña, M. M. Portillo, E. Peña-Cabrera, K. H. Pannell, J. Org. Chem. 2013, 78, 4245-4250
- (2013) J. Org. Chem. , vol.78 , pp. 4245-4250
- Roacho, R.I.¹ Metta-Magaña, A.² Portillo, M.M.³ Peña-Cabrera, E.⁴ Pannell, K.H.⁵

50
- 84897744998
- N. Boens, L. Wang, V. Leen, P. Yuan, B. Verbelen, W. Dehaen, M. Van der Auweraer, W. D. De Borggraeve, L. Van Meervelt, J. Jacobs, D. Beljonne, C. Tonnelé, R. Lazzaroni, M. J. Ruedas-Rama, A. Orte, L. Crovetto, E. M. Talavera, J. M. Alvarez-Pez, J. Phys. Chem. A 2014, 118, 1576-1594.
- (2014) J. Phys. Chem. A , vol.118 , pp. 1576-1594
- Boens, N.¹ Wang, L.² Leen, V.³ Yuan, P.⁴ Verbelen, B.⁵ Dehaen, W.⁶ Van Der Auweraer, M.⁷ De Borggraeve, W.D.⁸ Van Meervelt, L.⁹ Jacobs, J.¹⁰ Beljonne, D.¹¹ Tonnelé, C.¹² Lazzaroni, R.¹³ Ruedas-Rama, M.J.¹⁴ Orte, A.¹⁵ Crovetto, L.¹⁶ Talavera, E.M.¹⁷ Alvarez-Pez, J.M.¹⁸

51
- 27744542623
- H. L. Kee, C. Kirmaier, L. Yu, P. Thamyongkit, W. J. Youngblood, M. E. Calder, L. Ramos, B. C. Noll, D. F. Bocian, W. R. Scheidt, R. R. Birge, J. S. Lindsey, D. Holten, J. Phys. Chem. B 2005, 109, 20433-20443.
- (2005) J. Phys. Chem. B , vol.109 , pp. 20433-20443
- Kee, H.L.¹ Kirmaier, C.² Yu, L.³ Thamyongkit, P.⁴ Youngblood, W.J.⁵ Calder, M.E.⁶ Ramos, L.⁷ Noll, B.C.⁸ Bocian, D.F.⁹ Scheidt, W.R.¹⁰ Birge, R.R.¹¹ Lindsey, J.S.¹² Holten, D.¹³

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