10.1002/chem.201905597
Chemistry - A European Journal
COMMUNICATION
[3]
[4]
a) L. R. MacGillivray, G. S. Papaefstathiou, T. Friscic, T. D. Hamilton, D.
K. Bucar, Q. Chu, D. B. Varshney, I. G. Georgiev, Acc. Chem. Res. 2008,
41, 280; b) K. Biradha, R. Santra, Chem. Soc. Rev. 2013, 42, 950.
a) B. R. Bhogala, B. Captain, A. Parthasarathy, Ramamurthy, V. J. Am.
Chem. Soc. 2010, 132, 13434; b) M. Linares, A. Briceno, New J. Chem.
2010, 34, 587; c) A. L. Grobelny, N. P. Rath, R. H. Groeneman,
Photochem. Photobiol. Sci. 2019, 18, 989; d) G. Campillo-Alvarado, A.
D. Brannan, D. C. Swenson, L. R. MacGillivray, Org. Lett. 2018, 20,
5490; e) K. Tsaggeos, N. Masiera, A. Niwicka, V. Dokorou, M. G. Siskos,
S. Skoulika, A. Michaelides, Crystal Growth Des. 2012, 12, 2187; f) A.
Garai, K. Biradha, Crystal Growth Des. 2019, 19, 4602; g) S.
Bhattacharya, J. Stojakovic, B. K. Saha, L. R. MacGillivray Org. Lett.
2013, 15, 744; h) G. Ortega, J. Hernandez, T. Gonzalez, R. Dorta, A.
Briceno, Photochem. Photobiol. Sci. 2018, 17, 670; i) M. Gan, J. Yu, Y.
Wang, Y. Han, Crystal Growth Des. 2018, 18, 553; j) C. M. Santana, E.
W. Reinheimer, Jr. H. R. Krueger, L. R. MacGillivray, R. H. Groeneman,
Crystal Growth Des. 2017, 17, 2054; k) M. A. Sinnwell, J. N. Blad, L. R.
Thomas, L. R. MacGillivray, IUCrJ 2018, 5, 491; l) A. L. Grobelny, F. A.
Verdu, R. H. Groeneman, CrystEngComm 2017, 19, 3562; m) L. G.
Kuz’mina, A. I. Vedernikov, J. A. K. Howard, E. K. Lermontova, A. V.
Churakov, M. V. Alfimov, S. P. Gromov, J. Struct. Chem. 2014, 55, 1484;
n) K. M. Hutchins, J. C. Sumrak, D. C. Swenson, L. R. MacGillivray.
CrystEngComm 2014, 16, 5762; o) E. Elacqua, P. Kaushik, R. H.
Groeneman, J. C. Sumrak, D. Bucar, L. R. MacGillivray, Angew. Chem.
Int. Ed. 2012, 51, 1037.
[2+2] photodimerization proceeded for the photoactive cocrystals,
new equilibria will be established to rearrange photoinactive
cocrystals into inactive one and subsequently into photoadduct.
By this way, the conditions for [2+2] photodimerization would be
less strict, which requires only a tiny amount of photoinactive
cocrystals.
In conclusion, we have reported here
a simple and
straightforward strategy for rapid screening of additive for
selective [2+2] photodimerization of stilbazoles by implementation
of irradiation on a mixture of stilbazoles and carboxylic acid
additive suspended in a non-polar or moderately polar solvents.
Having identified oxalic acid as an excellent additive for most
cases, we applied this transformation to a wide range of
structurally diverse stilbazoles. Particularly interesting was the
ability of our strategy to apply to solid, waxy, amorphous, liquid or
even insoluble stilbazoles, making it more powerful to traditional
methods. In most cases, the purification of the expected adducts
as single isomers in clean reaction mixtures relied principally on
the removal of oxalic acid by simply washing with an aqueous
solution of NaHCO3. The potential in application to polar olefins
bearing many hydrogen bond forming sites has been
demonstrated successfully with stilbazoles bearing
a free
[5]
[6]
Photoactive cocrystals between some stilbazoles and fumaric or maleic
acid was described to be possible in methanol. The yields of the
corresponding [2+2] photocycloaddtion was shown to be enhanced by
grinding assistance in the presence of the solvent prior to the irradiation:
A. Briceno, D. Leal, G. Ortega, G. Dıaz de Delgado, E. Ocandoa L.
Cubillana, CrystEngComm 2013,15, 2795.
carboxylic acid group as well as some b-hetarylacrylic acids such
as 4-azacinnamic acid, b-(2-quinolyl)acrylic acid and urocanic
acid. From a more general perspective, we envision that the
operational simplicity, broad scope, low cost and scalability of this
strategy make it undoubtedly suitable for application in both
laboratory and industrial scales.
a) F. L. Hu, Y. Mi, C. Zhu, B. F. Abrahams, P. Braunstein, J. P. Lang,
Angew. Chem. Int. Ed. 2018, 57, 12696; b) Z. Ma, S. Yang, L. Zheng, B.
K. Teo, Crystal Growth Des 2019, 19, 3113; c) M. F. Wang, Y. Mi, F. L.
Hu, Z. Niu, X. H. Yin, Q. Huang, H. F. Wang, J. P. Lang, J. Am. Chem.
Soc. 2020, DOI: 10.1021/jacs.9b12358; d) X. X. Shi, W. H. Zhang, B. F.
Abrahams, P. Braunstein, J. P. Lang, Angew. Chem. Int. Ed. 2019, 58,
9453, e) D. Liu; Z. G. Ren, H. X. Li, J. P. Lang, N. Y. Li, B. F. Abrahams,
Angew. Chem. Int. Ed. 2010, 49, 4767; f) F. L. Hu, H. F. Wang, D. Guo,
H. Zhang, J. P. Lang, J. E. Beves, Chem. Commun. 2016, 52, 7990; g)
N. Y. Li., D. Liu.Z. G. Ren, C. Lollar, J. P. Lang, H. C. Zhou, Inorg. Chem.
2018, 57, 849.
Experimental Section
A mixture of olefin A (0.2 mmol) and oxalic acid dihydrate (40 mg, 0.32
mmol) in cyclohexane (2 mL) in a 7-mL Pyrex tube was stirred in the
photoreactor described in the Supporting Information for 16 h (unless
otherwise noted). After removal of cyclohexane, the solid crude reaction
mixture was stirred with CH2Cl2 (2 mL) and neutralized with an aqueous
saturated NaHCO3 solution (2-4 mL). The CH2Cl2 layer was separated, the
aqueous layer was extracted with CH2Cl2 (2 mL ´ 3). The combined
organic layers were filtered through a short pad of solid NaHCO3 to afford
the desired adduct. See Supporting information for more detail.
[7]
a) D. Liu, J. Lang, CrystEngComm 2014, 16, 76; b) J. H. Lee, S. Park, S.
Jeoung, H. R. Moon, CrystEngComm 2017, 19, 3719; c) F. Hu, S. Wang,
B. F. Abrahams, J. Lang, CrystEngComm 2015, 17, 4903; d) R.
Medishetty, Z. Bai, H. Yang, M. W. Wong, J. J. Vittal, Crystal Growth Des.
2015, 15, 4055; c) R. Medishetty, R. Tandiana, J. Wu, Z. Bai, Y. Du, J. J.
Vittal, Chem. Eur. J. 2015, 21, 11948; d) R. Medishetty, A. Husain, Z. Bai,
T. Runcevski, R. E. Dinnebier, P. Naumov, J. J. Vittal, Angew. Chem. Int.
Ed. 2014, 53, 5907; e) R. Medishetty, T. T. S. Yap, L. L. Koh, J. J. Vittal,
Chem. Commun. 2013, 49, 9567; f) R. Medishetty, L. L. Koh, G. K. Kole,
J. J. Vittal, Angew. Chem. Int. Ed. 2011, 50, 10949; g) K. Yadava, J. J.
Vittal, Chem. Eur. J. 2019, 25, 10394; h) J. Chen, Y. Hou, Q. Zhou, H.
Zhang, D. Liu. CrystEngComm 2017, 19, 2603; i) G. Li, W. Yin, G. Liu, L.
Ma, L. Huang, L. Li, L. Wang, Inorg. Chem. Commun. 2014, 43, 165; j)
D. Liu, J. Lang, B. F. Abrahams, Chem. Commun. 2013, 49, 2682.
a) S. Yamada, N. Uematsu, K. Yamashita, J. Am. Chem. Soc. 2007, 129,
12100; b) S. Yamada, Y. Nojiri, Chem. Commun. 2011, 47, 9143; c) B.
Mondal, T. Zhang, R. Prabhakar, B. Captain, V. Ramamurthy,
Photochem. Photobiol. Sci. 2014, 13, 1509; c) L. G. Kuz’mina, A. I.
Vedernikov, S. K. Sazonov, N. A. Lobova, A. V. Churakov, E. K.
Lermontova, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Russian
Chem. Bull. 2011, 60, 1734; d) S. Yamada, Y. Nojiri, M. Sugawara,
Tetrahedron Lett. 2010, 51, 2533; e) X. Li, L. Wu, L. Zhang, C. Tung, Org.
Lett. 2002, 4, 1175; f) K. Takagi, H. Usami, T. Shiichi, Y. Sawaki, Mol.
Cryst. Liq. Cryst. Sci. Tech. A 1992, 218, 109; f) H. Usami, K. Takagi, Y.
Sawaki, J. Chem. Soc. Perkin Trans. 2 1990, 10, 1723; g) K. Takagi, B.
R. Suddaby, S. L. Vadas, C. A. Backer, D. G. Whitten, J. Am. Chem. Soc.
1986, 108, 7865; h) M. Horner, S. Hünig, Liebigs Ann. Chem. 1982,
Acknowledgements
TB Nguyen thanks Engr. Nguyen Xuan Bong for all his support
and encouragement throughout this work. We thank Dr. A.
Marinetti (ICSN-CNRS) for her helpful support. Financial support
from Merlion program of the Embassy of France in Singapore to
initiate the collaboration between TB Nguyen and TM Nguyen is
gratefully acknowledged.
[8]
Keywords: solid state photodimerization • stilbazole •
cyclobutane • keyword 4 • keyword 5
[1]
[2]
J. Vansant, S. Toppet, G. Smets, J. P. Declercq, G. Germain, M. Van
Meerssche, J. Org. Chem. 1980, 45, 1565.
a) M. D. Cohen, G. M. J. Schmidt, F. I. Sonntag, J. Chem. Soc. 1964,
2000; b) G. M. J. Schmidt, Pure Appl. Chem. 1971, 27, 647; b) V.
Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433.
This article is protected by copyright. All rights reserved.