Please do not adjust margins
Green Chemistry
Page 4 of 5
DOI: 10.1039/C8GC00117K
COMMUNICATION
Journal Name
(r) M. Marz, J. Chudoba, M. Kohout and R. Cibulka, Org.
Biomol. Chem., 2017, 15, 1970.
For examples of the cooperative catalysis of flavins, see: (a)
oxygen as the only sacrificial reagent, thus generating
environmentally benign H2O as the lone byproduct. Because of
the unique multiple catalytic roles of flavin, the reaction rate
of sulfenylation with thiol was enhanced in comparison to that
with disulfide. The present coupled organocatalysis system will
provide new paradigms for novel green aerobic
transformations using multiple catalytic systems.
5
Y. Yano, Y. Hoshino and W. Tagaki, Chem. Lett., 1980, 9, 749;
(b) S. Shinkai, T. Yamashita, Y. Kusano and O. Manabe, J. Org.
Chem., 1980, 45, 4947; (c) K. Bergstad, S. Y. Jonsson and J.-E.
Bäckvall, J. Am. Chem. Soc., 1999, 121, 10424 and refs. 4e, m,
and p–r.
T. Ishikawa, M. Kimura, T. Kumoi and H. Iida, ACS Catal.,
2017, 4986.
F. Müller, in Chemistry and Biochemistry of Flavoenzymes,
CRC Press, Boston, 1991.
(a) I. M. Gascoigne and G. K. Radda, Biochim. Biophys. Acta
Bioenerg., 1967, 131, 498; (b) M. J. Gibian and D. V.
Winkelman, Tetrahedron Lett., 1969, 10, 3901; (c) E. L.
6
7
8
Conflicts of interest
There are no conflicts to declare.
Loechler and T. C. Hollocher, J. Am. Chem. Soc., 1975, 97
,
Acknowledgements
3235; (d) I. Yokoe and T. C. Bruice, J. Am. Chem. Soc., 1975,
97, 450; (e) Y. Yano, M. Nakazato and E. Ohya, J. Chem. Soc.
Perkin Trans. II, 1985, 77; (f) W.-S. Li, N. Zhang and L. M.
Sayre, Tetrahedron, 2001, 57, 4507.
This work was supported in part by JSPS KAKENHI (Grant-in-Aid
for Scientific Research (C), no. 16K05797) and the Shorai
Foundation for Science and Technology. This work was
performed in part under the Cooperative Research Program of
the Institute for Protein Research, Osaka University, CR-17-05.
9
(a) R. Sundberg, in Indoles, Academic Press, London, 1996;
,
(b) G. R. Humphrey and J. T. Kuethe, Chem. Rev., 2006, 106
2875.
10 (a) M. Bandini and A. Eichholzer, Angew. Chem. Int. Ed.,
2009, 48, 9608; (b) A. H. Sandtorv, Adv. Synth. Catal., 2015,
357, 2403.
11 (a) M. Raban and L. J. Chern, J. Org. Chem., 1980, 45, 1688;
(b) P. Hamel, J. Org. Chem., 2002, 67, 2854; (c) M. Matsugi,
K. Murata, K. Gotanda, H. Nambu, G. Anilkumar, K.
Matsumoto and Y. Kita, J. Org. Chem., 2001, 66, 2434; (d) Q.
Wu, D. Zhao, X. Qin, J. Lan and J. You, Chem. Commun., 2011,
47, 9188; (e) M. Chen, Z.-T. Huang and Q.-Y. Zheng, Chem.
Commun., 2012, 48, 11686; (f) W. L. Ge and Y. Y. Wei, Green
Chem., 2012, 14, 2066; (g) D. Huang, J. Chen, W. Dan, J. Ding,
M. Liu and H. Wu, Adv. Synth. Catal., 2012, 354, 2123; (h) G.
La Regina, V. Gatti, V. Famiglini, F. Piscitelli and R. Silvestri,
ACS Combinatorial Sci., 2012, 14, 258; (i) F.-L. Yang and S.-K.
Tian, Angew. Chem. Int. Ed., 2013, 52, 4929; (j) F. H. Xiao, H.
Notes and references
1
(a) C. L. Hill, Nature, 1999, 401, 436; (b) L. I. Simándi, in
Advances in Catalytic Activation of Dioxygen by Metal
Complexes, Kluwer Academic Publishers, Dordrecht, The
Netherlands, 2002; (c) J.-E. Bäckvall, in Modern Oxidation
Methods, Wiley-VCH, Weinheim, 2004.
2
3
J. Piera and J.-E. Bäckvall, Angew. Chem., Int. Ed., 2008, 47,
3506.
(a) Y. Imada and T. Naota, Chem. Rec., 2007,
Gelalcha, Chem. Rev., 2007, 107, 3338; (c) G. de Gonzalo and
M. W. Fraaije, ChemCatChem, 2013, , 403; (d) H. Iida, Y.
7, 354; (b) F. G.
5
Imada and S.-I. Murahashi, Org. Biomol. Chem., 2015, 13
7599.
,
Xie, S. W. Liu and G. J. Deng, Adv. Synth. Catal., 2014, 356
,
364; (k) H. Qi, T. X. Zhang, K. F. Wan and M. M. Luo, J. Org.
Chem., 2016, 81, 4262; (l) J. X. Li, C. S. Li, S. R. Yang, Y. N. An,
W. Q. Wu and H. F. Jiang, J. Org. Chem., 2016, 81, 7771; (m)
Y. Yang, S. Zhang, L. Tang, Y. B. Hu, Z. G. Zha and Z. Y. Wang,
Green Chem., 2016, 18, 2609.
4
For recent examples of flavin-catalyzed oxidative
transformations with molecular oxygen, see: (a) Y. Imada, H.
Iida, S. Ono and S. I. Murahashi, J. Am. Chem. Soc., 2003,
125, 2868; (b) Y. Imada, H. Iida, S.-I. Murahashi and T. Naota,
Angew. Chem., Int. Ed., 2005, 44, 1704; (c) Y. Imada, H. Iida
and T. Naota, J. Am. Chem. Soc., 2005, 127, 14544; (d) J. F.
Teichert, T. den Hartog, M. Hanstein, C. Smit, B. ter Horst, V.
Hernandez-Olmos, B. L. Feringa and A. J. Minnaard, ACS
12 (a) Y. Maeda, M. Koyabu, T. Nishimura and S. Uemura, J. Org.
Chem., 2004, 69, 7688; (b) J. A. Campbell, C. A. Broka, L.
Gong, K. A. M. Walker and J. H. Wang, Tetrahedron Lett.,
2004, 45, 4073; (c) K. M. Schlosser, A. P. Krasutsky, H. W.
Catal., 2011, 1, 309; (e) S. Iwahana, H. Iida and E. Yashima,
Hamilton, J. E. Reed and K. Sexton, Org. Lett., 2004, 6, 819;
Chem. Eur. J., 2011, 17, 8009; (f) S. Chen and F. W. Foss, Org.
Lett., 2012, 14, 5150; (g) S. Chen, M. S. Hossain and F. W.
Foss, Org. Lett., 2012, 14, 2806; (h) Y. Imada, T. Kitagawa, H.-
K. Wang, N. Komiya and T. Naota, Tetrahedron Lett., 2013,
54, 621; (i) S. Chen, M. S. Hossain and F. W. Foss, ACS Sus.
(d) J. S. Yadav, B. V. S. Reddy and Y. J. Reddy, Tetrahedron
Lett., 2007, 48, 7034; (e) G. Wu, J. Wu, J. Wu and L. Wu,
Synth. Commun., 2008, 38, 1036; (f) J. S. Yadav, B. V. S.
Reddy, Y. J. Reddy and K. Praneeth, Synthesis, 2009, 1520; (g)
X. Zhang, X. Zhou, H. Xiao and X. Li, RSC Adv., 2013,
(h) Y. Liu, Y. Zhang, C. Hu, J.-P. Wan and C. Wen, Rsc Adv.,
2014, , 35528; (i) H. Zhang, X. Bao, Y. Song, J. Qu and B.
Wang, Tetrahedron, 2015, 71, 8885; (j) X. Liu, H. Cui, D. Yang,
S. Dai, G. Zhang, W. Wei and H. Wang, Catal. Lett., 2016, 146
3, 22280;
Chem. Eng., 2013, 1, 1045; (j) S.-I. Murahashi, D. Zhang, H.
Iida, T. Miyawaki, M. Uenaka, K. Murano and K. Meguro,
Chem. Commun., 2014, 50, 10295; (k) H. Kotoučová, I.
Strnadová, M. Kovandová, J. Chudoba, H. Dvořáková and R.
Cibulka, Org. Biomol. Chem., 2014, 12, 2137; (l) A. T. Murray,
M. J. H. Dowley, F. Pradaux-Caggiano, A. Baldansuren, A. J.
Fielding, F. Tuna, C. H. Hendon, A. Walsh, G. C. Lloyd-Jones,
M. P. John and D. R. Carbery, Angew. Chem. Int. Ed., 2015,
54, 8997; (m) B. Muhldorf and R. Wolf, Angew. Chem. Int.
Ed., 2016, 55, 427; (n) T. Neveselý, E. Svobodová, J. Chudoba,
M. Sikorski and R. Cibulka, Adv. Synth. Cat., 2016, 358, 1654;
(o) T. Hartman and R. Cibulka, Org. Lett., 2016, 18, 3710; (p)
C. J. Zhu, Q. Li, L. L. Pu, Z. T. Tan, K. Guo, H. J. Ying and P. K.
4
,
1743; (k) Saima, D. Equbal, A. G. Lavekar and A. K. Sinha, Org.
Biomol. Chem., 2016, 14, 6111; (l) S. Yi, M. Li, W. Mo, X. Hu,
B. Hu, N. Sun, L. Jin and Z. Shen, Tetrahedron Lett., 2016, 57
1912; (m) W. Guo, W. Tan, M. Zhao, K. Tao, L.-Y. Zheng, Y.
Wu, D. Chen and X.-L. Fan, Rsc Adv., 2017, , 37739
,
7
13 (a) K. Keller, Chem. Ber., 1913, 46, 726; (b) W. Noland and W.
Kuryla, J. Org. Chem., 1960, 25, 486; (c) R. J. Sundberg, in The
Chemistry of Indoles, Academic Press, New York, 1970.
14 T. C. Bruice, J. B. Noar, S. S. Ball and U. V. Venkataram, J. Am.
Chem. Soc., 1983, 105, 2452.
Ouyang, ACS Catal., 2016, 6, 4989; (q) T. Hering, B. Muhldorf,
R. Wolf and B. König, Angew. Chem. Int. Ed., 2016, 55, 5342;
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins