E
J. Nandi et al.
Letter
Synlett
R
N
SO4
4
AcHN
N
N
–
OH
HSO4
5
HAT
H
H
N
O
NH3
R
R
H
6
3
ACT cycle
AcHN
AcHN
N
N
O
O
2
1
SET
[Ru]2+
[Ru]3+
7
9
Photocatalytic Cycle
SO4
+
hv
SET
2–
SO4
*[Ru]2+
2–
S2O8
8
Scheme 4 Plausible reaction pathway
(4) For reviews of metal-catalyzed approaches, see: (a) Anbarasan,
P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
(b) Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87,
779.
(5) (a) Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans,
J.; Weiss, S.; Beller, M. Chem. Eur. J. 2003, 9, 1828. (b) Kim, J.;
Kim, H. J.; Chang, S. Angew. Chem. Int. Ed. 2012, 51, 11948.
(c) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.;
Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177.
(6) For initial reports, see: (a) Schareina, T.; Zapf, A.; Beller, M.
Chem. Commun. 2004, 12, 1388. (b) Weissman, S. A.; Zewge, D.;
Chen, C. J. Org. Chem. 2005, 70, 1508. For examples, see:
(c) Richardson, J.; Mutton, S. P. J. Org. Chem. 2018, 83, 4922.
(d) Senecal, T. D.; Shu, W.; Buchwald, S. L. Angew. Chem. Int. Ed.
2013, 52, 10035.
(10) (a) Mercadante, M. A.; Kelly, C. B.; Bobbitt, J. M.; Tilley, L. J.;
Leadbeater, N. E. Nat. Protoc. 2013, 8, 666. (b) Kelly, C. B.;
Mercadante, M. A.; Wiles, R. J.; Leadbeater, N. E. Org. Lett. 2013,
15, 2222. (c) Bobbitt, J. M.; Bartelson, A. L.; Bailey, W. F.; Hamlin,
T. A.; Kelly, C. B. J. Org. Chem. 2014, 79, 1055. (d) Hamlin, T. A.;
Kelly, C. B.; Leadbeater, N. E. Eur. J. Org. Chem. 2013, 3658.
(e) Kelly, C. B.; Mercadante, M. A.; Hamlin, T. A.; Fletcher, M. H.;
Leadbeater, N. E. J. Org. Chem. 2012, 77, 8131. (f) Eddy, N. A.;
Kelly, C. B.; Mercadante, M. A.; Leadbeater, N. E.; Fenteany, G.
Org. Lett. 2012, 14, 498. (g) Pradhan, P. P.; Bobbitt, J. M.; Bailey,
W. F. J. Org. Chem. 2009, 74, 9524. (h) Qui, J.; Pradhan, P. P.;
Blanck, N. B.; Bobbitt, J. M.; Bailey, W. F. Org. Lett. 2012, 14, 350.
(i) Ovian, J. M.; Kelly, C. B.; Pistritto, V. A.; Leadbeater, N. E. Org.
Lett. 2017, 19, 1286. (j) Miller, S. A.; Bobbitt, J. M.; Leadbeater, N.
E. Org. Biomol. Chem. 2017, 15, 2817.
(7) (a) Lambert, K. M.; Bobbitt, J. M.; Eldirany, S. A.; Wiberg, K. B.;
Bailey, W. F. Org. Lett. 2014, 16, 6484. (b) Kim, J.; Stahl, S. S. ACS
Catal. 2013, 3, 1652. (c) Lambert, K. M.; Bobbitt, J. M.; Eldirany,
S. A.; Kissane, L. E.; Sheridan, R. K.; Stempel, Z. D.; Sternberg
Francis, H.; Bailey, W. F. Chem. Eur. J. 2016, 22, 5156.
(8) (a) Dornan, L. M.; Cao, Q.; Flanagan, J. C. A.; Crawford, J. J.; Cook,
M. J.; Muldoon, M. J. Chem. Commun. 2013, 49, 6030. (b) Tao, C.;
Liu, F.; Zhu, Y.; Liu, W.; Cao, Z. Org. Biomol. Chem. 2013, 11,
3349. (c) Yin, W.; Wang, C.; Huang, Y. Org. Lett. 2013, 15, 1850.
(d) Oishi, T.; Yamaguchi, K.; Mizuno, N. Angew. Chem. Int. Ed.
2009, 48, 6286. (e) Capdevielle, P.; Lavigne, A.; Maumy, M. Syn-
thesis 1989, 451. (f) Fang, C.; Li, M.; Hu, X.; Mo, W.; Hu, B.; Sun,
N.; Jin, L.; Shen, Z. Adv. Synth. Catal. 2016, 358, 1157.
(11) Kelly, C. B.; Lambert, K. M.; Mercadante, M. A.; Ovian, J. M.;
Bailey, W. F.; Leadbeater, N. E. Angew. Chem. Int. Ed. 2015, 54,
4241.
(12) See, for example: (a) Ciriminna, R.; Pagliaro, M. Org. Process Res.
Dev. 2010, 14, 245. (b) Ciriminna, R.; Pagliaro, M. Org. Process
Res. Dev. 2010, 14, 245.
(13) Noh, J.; Kim, J. J. Org. Chem. 2015, 80, 11624.
(14) For reviews, see: (a) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.;
Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 52.
(b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
(c) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem.
2016, 81, 6898. (d) Prier, C. K.; Prier Rankic, D. A.; Macmillan, D.
W. C. Chem. Rev. 2013, 113, 5322.
(9) For reviews, see: (a) Leadbeater, N. E.; Bobbitt, J. M. Aldrichimica
Acta 2014, 47, 65. (b) Kelly, C. B. Synlett 2013, 24, 527.
(c) Bobbitt, J. M.; Bruckner, C.; Merbouh, N. Org. React. 2010, 74,
103.
(15) Pistritto Vincent, A.; Paolillo, J. M.; Bisset, K. A.; Leadbeater, N. E.
Org. Biomol. Chem. 2018, 16, 4715.
(16) Nandi, J.; Ovian, J. M.; Kelly, C. B.; Leadbeater, N. E. Org. Biomol.
Chem. 2017, 15, 8295.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–F