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COMMUNICATION
Journal Name
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chromanones with high diastereocontrol and up to 93% isolated
yield. Finally, the MFP protocol is readily amenable to large-
scale synthesis as demonstrated for a 12 h continuous-flow
Montero De Espinosa, M. A. R. Meier and C. Barner-Kowollik,
DOI: 10.1039/C8CC01373J
Macromolecules, 2012, 45
,
5012-5019; (b) K. K.
Oehlenschlaeger, J. O. Mueller, N. B. Heine, M. Glassner, N. K.
Guimard, G. Delaittre, F. G. Schmidt and C. Barner-Kowollik,
Angew. Chem., Int. Ed., 2013, 52, 762-766.
synthesis of chromanone 3g
.
0 (a) X. Yuan, S. Dong, Z. Liu, G. Wu, C. Zou and J. Ye, Org. Lett.,
This work was supported by the CariParo Foundation with
AMYCORES starting grant (to L.D.), project CPDA141843/14 of
Università di Padova (to T. C.) and MIUR. Prof. Andrea Sartorel
and Giulia Alice Volpato are gratefully acknowledged for
measuring the light sources emission spectra. Andrea Faresin,
Alberto Doimo and Stefano Mercanzin are gratefully
acknowledged for technical assistance.
2
017, 19, 2322-2329; (b) L. Dell’Amico, V. M. Fernández-
Alvarez, F. Maseras and P. Melchiorre, Angew. Chem., Int. Ed.,
017, 56, 3304-3308.
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1 T. Ide, S. Masuda, Y. Kawato, H. Egami and Y. Hamashima, Org.
Lett., 2017, 19, 4452-4455.
2 Y. Masuda, N. Ishida and M. Murakami, J. Am. Chem. Soc.,
2
015, 137, 14063-14066.
3 The MFP is composed by a PTFE tubing (100 cm length, 0.75
mm internal diameter, 1.58 mm O.D.), wrapped around the
two branches of a U-shaped, 9W, bulb lamp having the
emission maximum centred at 365 nm.
Conflicts of interest
There are no conflicts to declare.
14 All the batch reactions were performed with same apparatus
and illuminated with the same light-source employed for the
MFP setup and stopped when full conversion was observed by
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H-NMR analysis of the crude reaction mixture. See ESI for
details.
Notes and references
15 Due to the improved performances of the MFP it was possible
to use cheaper commercially available Togni’s reagent I. In the
described method Togni’s reagent II was used. See reference
1
For a general review see e.g.: (a) M. Fagnoni, D. Dondi, D.
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1 for details.
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1
6 To compare the developed MFP methodology with already
reported protocols see table S3 in the ESI.
9
913.
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3
(a) M. H. Shaw, J. Twilton and D. W. C. MacMillan, J. Org.
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7 For selected reviews on the biological activity of coumarines
see e.g.: (a) C. A. Kontogiorgis and D. J. Hadjipavlou-Litina, J.
Med. Chem., 2005, 48, 6400-6408; (b) F. G. Medina, J. G.
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Prod. Rep., 2015, 32, 1472-1507; (c) V. Mandlik, S. Patil, R.
Bopanna, S. Basu and S. Singh, PLoS One, 2016, 11, 1-15.
8 For selected reviews on the biological activity of chromanones
see e.g.: (a) L. Feng, M. M. Maddox, M. Z. Alam, L. S. Tsutsumi,
G. Narula, D. F. Bruhn, X. Wu, S. Sandhaus, R. B. Lee, C. J.
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Med. Chem., 2014, 57, 8398-8420; (b) B. Mayuri, P. Kavitha, S.
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890; (b) Y.-Q. Zou, F. M. Hörmann and T. Bach, Chem. Soc.
Rev., 2018, 47, 278-290.
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(a) L. D. Elliott, J. P. Knowles, P. J. Koovits, K. G. Maskill, M. J.
Ralph, G. Lejeune, L. J. Edwards, R. I. Robinson, I. R. Clemens,
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M. B. Plutschack, B. Pieber, K. Gilmore and P. H. Seeberger,
Chem. Rev., 2017, 117, 11796-11893; (c) D. Cambié, C.
Bottecchia, N. J. W. Straathof, V. Hessel and T. Noël, Chem.
Rev., 2016, 116, 10276-10341.
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145, 1-9.
9 For selected studies on light-promoted self [2+2]-
cycloaddition of coumarins see: (a) T. Wolff and H. Görner,
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(a) Y. Su, K. Kuijpers, V. Hessel and T. Noël, React. Chem. Eng.,
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016, 1, 73-81; (b) Y. Su, N. J. W. Straathof, V. Hessel and T.
Phys. Chem. Chem. Phys., 2004,
Scheller, O. Rademacher and T. Wolff, J. Org. Chem., 2003, 68
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Noël, Chem. - Eur. J., 2014, 20, 10562-10589; (c) N. J. W.
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0-21; (d) Z. J. Garlets, J. D. Nguyen and C. R. J. Stephenson,
,
,
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and J. Sivaguru, Chem. Commun., 2010, 46, 225-227; (d) D. V.
Rao, H. Ulrich, F. A. Stuber and A. A. R. Sayigh, Chem. Ber.,
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Stephenson, J. Org. Chem., 2012, 77, 1617–1622.
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973, 106, 388-395.
0 Under MFP conditions, cyclobutane
decomposing to 2g. Control experiments rule out a direct
addition of photoenol A' to cyclobutane
(a) N. C. Yang, C. Rivas, J. Am. Chem. Soc. 1961, 83, 2213-2213;
2
2
4 is not reversibly
(
b) P. Klán, J. Wirz, A. Gudmundsdottir, in Photoenolization
and Its Applications, CRC Handbook of Organic
Photochemistry and Photobiology, ed. A. Griesbeck, CRC
4
.
1 To mesure the photon flow under both MFP and batch setups
the following reported method has been used: N. De la Cruz,
V. Romero, R. F. Dantas, P. Marco, B. Bayarri, J. Giménez, S.
Esplugas, Catal. Today, 2013, 209, 209-214. See ESI for
additional details.
rd
Press, United States, 3 ed., 2012, ch. 26, pp. 627-652; (c) B.
By Elliott, and R. Stevenson, J. Chem. Soc., Perkin Trans. 1,
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973, 308-313; (d) P. G. Sammes, Tetrahedron, 1976, 32, 405-
22; (e) B. Grosch, C. N. Orlebar, E. Herdtweck, W. Massa, T.
Bach, Angew. Chem., Int. Ed. 2003, 42, 3693-3696.
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(a) K. C. Nicolaou, D. Gray, J. Tae, Angew. Chem., Int. Ed., 2001,
40, 3675-3678; (b) K. C. Nicolaou, D. Gray, J. Tae, Angew.
Chem. Int., Ed. 2001, 40, 3679-3683; (c) K. C. Nicolaou, D. L. F.
Gray, J. Tae, J. Am. Chem. Soc. 2004, 126, 613-627. (d) L.
Dell’Amico, A. Vega-Peñaloza, S. Cuadros and P. Melchiorre,
Angew. Chem., Int. Ed., 2016, 55, 3313-3317.
K. Hiltebrandt, K. Elies, D. R. D’hooge, J. P. Blinco, C. Barner-
Kowollik, J. Am. Chem. Soc. 2016, 138, 7048-7054.
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