D
L.-M. Mohr, T. Bach
Letter
Synlett
tion of nitro compounds to amines,11c,14,29 the method offers
also access to various aminocyclobutanes. Mechanistically,
it remains open to what degree a charge transfer30 occurs
upon encounter of the photoexcited nitro compound and
the olefin. In addition, it might be worth to study whether
other nitroethenes but nitrostyrenes are equally suited for
[2+2] photocycloaddition reactions. Work along these lines
is in progress in our laboratories and will be reported in due
course.
(8) (a) Alonso, R.; Bach, T. Angew. Chem. Int. Ed. 2014, 53, 4368.
(b) Tröster, A.; Alonso, R.; Bauer, A.; Bach, T. J. Am. Chem. Soc.
2016, 138, 7808. (c) Blum, T. R.; Miller, Z. D.; Bates, D. M.; Guzei,
I. A.; Yoon, T. P. Science 2016, 354, 1391.
(9) (a) Guo, H.; Herdtweck, E.; Bach, T. Angew. Chem. Int. Ed. 2010,
49, 7782. (b) Brimioulle, R.; Bach, T. Science 2013, 342, 840.
(c) Brimioulle, R.; Bauer, A.; Bach, T. J. Am. Chem. Soc. 2015, 137,
5170. (d) Brenninger, C.; Pöthig, A.; Bach, T. Angew. Chem. Int.
Ed. 2017, 56, 4337.
(10) Reviews on the photochemistry of nitro compounds: (a) Ho, T.-
I.; Chow, Y. L. Photochemistry of Nitro and Nitroso Compounds, In
The Chemistry of Functional Groups, Supplement F2: The Chemis-
try of Amino, Nitroso, Nitro and Related Groups; Patai, S., Ed.;
Wiley: Chichester, 1996, 747. (b) Döpp, D. Photochemical Reac-
tivity of the Nitro Group, In CRC Handbook of Organic Photochem-
istry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC
Press: Boca Raton, 1995, 1019.
Funding Information
Financial support by the European Research Council under the Euro-
pean Union’s Horizon 2020 research and innovation programme
(grant agreement No 665951 – ELICOS) is gratefully acknowledged.
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(11) (a) Priebs, B. Justus Liebigs Ann. Chem. 1884, 225, 319.
(b) Meisenheimer, J.; Heim, F. Justus Liebigs Ann. Chem. 1907,
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(12) Chapman, O. L.; Griswold, A. A.; Hoganson, E.; Lenz, G.;
Reasoner, J. Pure Appl. Chem. 1964, 9, 585.
Supporting Information
Supporting information for this article is available online at
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(13) In a later paper, the reaction of trans-β-nitrostyrene (1) and 2,3-
dimethylbutadiene (2d) was reported to be performed at λ =
300 nm: Magner, J. T.; Selke, M.; Russell, A. A.; Chapman, O. L.
J. Chem. Ed. 1996, 73, 854.
(14) Majima, T.; Pac, C.; Sakurai, H. J. Am. Chem. Soc. 1980, 102, 5265.
(15) Ramkumar, D.; Sankararaman, S. J. Chem. Soc., Perkin Trans. 2
1996, 939.
Primary Data
nect.com/products/ejournals/journal/10.1055/s-00000083 and
can be cited using the following DOI: 10.4125/pd0095th.
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(16) For a Cr-photocatalytic [4+2] cycloaddition of trans-β-nitro-
para-methoxystyrene and 1,3-dienes, see: Stevenson, S. M.;
Higgins, R. F.; Shores, M. P.; Ferreira, E. M. Chem. Sci. 2017, 8,
654.
(17) (a) Cheng, L. T.; Tam, W.; Marder, S. R.; Stiegman, A. E.; Rikken,
G.; Spangler, C. W. J. Phys. Chem. 1991, 95, 10643.
(b) Aboskalova, N. I.; Smirnova, N. N.; Kataeva, O. N.; Baichurin,
R. I.; Fel'gendler, A. V.; Berkova, G. A.; Berestovitskaya, V. A. Russ.
J. Gen. Chem. 2008, 78, 1711.
References and Notes
(1) Poplata, S.; Tröster, A.; Zou, Y.-Q.; Bach, T. Chem. Rev. 2016, 116,
9748.
(2) Roth, H. D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1193.
(3) (a) Lennartson, A.; Roffey, A.; Moth-Poulsen, K. Tetrahedron Lett.
2015, 56, 1457. (b) Dubonosov, A. D.; Bren, V. A.; Chernoivanov,
V. A. Russ. Chem. Rev. 2002, 71, 917.
(4) (a) Barwise, A. J. G.; Gorman, A. A.; Leyland, R. L.; Smith, P. G.;
Rodgers, M. A. J. J. Am. Chem. Soc. 1978, 100, 1814. (b) Jones, G.
II.; Chiang, S.-H.; Xuan, P. T. J. Photochem. 1979, 10, 1.
(5) (a) Ikezawa, H.; Kutal, C.; Yasufuku, K.; Yamazaki, H. J. Am.
Chem. Soc. 1986, 108, 1589. (b) Grutsch, P. A.; Kutal, C. J. Am.
Chem. Soc. 1986, 108, 3108. (c) Sluggett, G. W.; Turro, N. J.; Roth,
H. D. J. Phys. Chem. A 1997, 101, 8834.
(6) (a) Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew.
Chem. Int. Ed. 2015, 54, 3872. (b) Meggers, E. Chem. Commun.
2015, 51, 3290.
(7) (a) Zou, Y.-Q.; Duan, S.-W.; Meng, X.-G.; Hu, X.-Q.; Gao, S.; Chen,
J.-R.; Xiao, W.-J. Tetrahedron 2012, 68, 6914. (b) Lu, Z.; Yoon, T. P.
Angew. Chem. Int. Ed. 2012, 51, 10329. (c) Kumarasamy, E.;
Raghunathan, R.; Jockusch, S.; Ugrinov, A.; Sivaguru, J. J. Am.
Chem. Soc. 2014, 136, 8729. (d) Hurtley, A. E.; Lu, Z.; Yoon, T. P.
Angew. Chem. Int. Ed. 2014, 53, 8991. (e) Liu, Q.; Zhu, F.-P.; Jin,
X.-L.; Wang, X.-J.; Chen, H.; Wu, L.-Z. Chem. Eur. J. 2015, 21,
10326. (f) Mojr, V.; Svobodová, E.; Straková, K.; Neveselý, T.;
Chudoba, J.; Dvořáková, H.; Cibulka, R. Chem. Commun. 2015, 51,
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(18) (a) Cowley, D. J. J. Chem. Soc., Perkin Trans. 2 1975, 1576.
(b) Zhang, S.-Q.; Wang, H.-G.; Pei, K.-M.; Zheng, X. J. Chem. Phys.
2007, 126, 194505.
(19) For further references to the photochemistry of nitroolefins,
see: (a) Ried, W.; Wilk, M. Justus Liebigs Ann. Chem. 1954, 590,
111. (b) Zimmerman, H. E.; Roberts, L. C.; Arnold, R. J. Org. Chem.
1977, 42, 621. (c) Humphry-Baker, R. A.; Salisbury, K.; Wood, G.
P. J. Chem. Soc., Perkin Trans. 2 1978, 659. (d) Grant, R. D.;
Pinhey, J. T.; Rizzardo, E.; Smith, G. C. Aust. J. Chem. 1985, 38,
1505. (e) Kassaee, M. Z.; Nassari, M. A. J. Photochem. Photobiol. A
2000, 136, 41.
(20) For the emission spectra of the lamps, see for λ = 300 nm, 366
nm: (a) Maturi, M. M.; Wenninger, M.; Alonso, R.; Bauer, A.;
Pöthig, A.; Riedle, E.; Bach, T. Chem. Eur. J. 2013, 19, 7461. λ =
350 nm: (b) Rimböck, K.-H.; Pöthig, A.; Bach, T. Synthesis 2015,
47, 2869. λ = 419 nm: (c) Alonso, R.; Bach, T. Angew. Chem. Int.
Ed. 2014, 53, 4368. λ = 457 nm, 470 nm: (d) Lenhart, D.; Bauer,
A.; Pöthig, A.; Bach, T. Chem. Eur. J. 2016, 22, 6519.
(21) Representative Procedure
29.8 mg of nitrostyrene 1 (199 μmol, 1.00 equiv) and 10.0 equiv
of olefin 2e (168 mg, 2.00 mmol) were dissolved in degassed,
dry CH2Cl2 (c = 20 mM). The reaction solution was irradiated at
Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E