Communication
Dalton Transactions
Ce(NO3)6 the yield lowered to 10%, while in the presence of
1 equiv. of K2S2O8 the yield lowered to 8%. A third possibility
is that the oxidation might be performed by DMSO. In biblio-
graphy there are reports of oxidations of Pt and other tran-
sition metal complexes performed by a molecule of DMSO,
which is reduced to SMe2.24 Theoretical calculations are under
way in order to clarify the mechanism.
In conclusion, we have found that like other transition
metal reagents, AgOAc is able to promote the oxidation of a
C–H bond at an allylic position. To the best of our knowledge
this is the first report on such reactivity with silver. The overall
process involves the oxidative cyclization of alkenoic acids
derived from salicylic acid and analogues to 4H-benzo[d][1,3]-
dioxin-4-ones. The experimental results disfavour the partici-
pation of radicals or Ag(II) species in the cyclization.
Tetrahedron Lett., 2014, 55, 2230–2232. Mn: T. K. M. Shing,
Y.-Y. Yeung and P. L. Su, Org. Lett., 2006, 8, 3149–3151. Co:
(d) J. A. R. Salvador and J. H. Clark, Chem. Commun., 2001,
33–34; (e) M. Jurado-Gonzalez, A. C. Sullivan and
J. R. Wilson, Tetrahedron Lett., 2003, 44, 4283–4286. Rh:
(f) A. J. Catino, R. E. Forslund and M. P. Doyle, J. Am.
Chem. Soc., 2004, 126, 13622–13623; (g) E. C. McLaughlin,
H. Choi, K. Wang, G. Chiou and M. P. Doyle, J. Org. Chem.,
2009, 74, 730–738.
3 (a) K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois and
M. C. White, J. Am. Chem. Soc., 2006, 128, 9032–9033;
(b) M. Bischop and J. Pietruszka, Synlett, 2011, 2689–2692.
4 (a) K. J. Fraunhoffer and M. C. White, J. Am. Chem. Soc.,
2007, 129, 7274–7276; (b) I. I. Strambeanu and
M. C. White, J. Am. Chem. Soc., 2013, 135, 12032–12037.
5 J. V. Crivello, Synth. Commun., 1976, 6, 543.
6 (a) Y. Cui and C. He, Angew. Chem., Int. Ed., 2004, 43, 4210–
4212; (b) Z. Li, D. A. Capretto, R. Rahaman and C. He,
Angew. Chem., Int. Ed., 2007, 46, 5184–5186;
(c) B. P. Gómez-Emeterio, J. Urbano, M. M. Díaz-Requejo
and P. J. Pérez, Organometallics, 2008, 27, 4126–4130;
(d) J. W. Rigoli, C. D. Weatherly, B. T. Vo, S. Neale,
A. R. Meis and J. M. Schomaker, Org. Lett., 2013, 15, 290–
293; (e) J. W. Rigoli, C. D. Weatherly, J. M. Alderson,
B. T. Vo and J. M. Schomaker, J. Am. Chem. Soc., 2013, 135,
17238–17241; (f) R. J. Scamp, J. W. Rigoli and
J. M. Schomaker, Pure Appl. Chem., 2014, 86, 381–393;
(g) J. M. Alderson, A. M. Phelps, R. H. Scamp, N. S. Dolan
and J. M. Schomaker, J. Am. Chem. Soc., 2014, 136, 16720–
16723; (h) M. Yang, B. Su, Y. Wang, K. Chen, X. Jiang,
Y.-F. Zhang, X.-S. Zhang, G. Chen, Y. Cheng, Z. Cao,
Q.-Y. Guo, L. Wang and Z.-J. Shi, Nat. Commun., 2014, 5,
4707; (i) J.-J. Dai, W.-T. Xu, Y.-D. wu, W.-M. Zhang, Y. Gong,
X.-P. He, X.-Q. Zhang and H.-J. Xu, J. Org. Chem., 2015, 80,
911–919.
Acknowledgements
This work was supported by CONACyT (153523), DGAPA
(IA201615) and I. Química. Carrillo-Arcos thanks CONACyT
(21455) and DGAPA for undergraduate fellowships. Rojas-
Ocampo thanks CONACyT for
a predoctoral fellowship
(574767). The authors would like to thank M. A. Peña-
González, E. Huerta-Salazar, B. Quiroz-García, I. Chávez-Uribe,
M. R. Patiño-Maya, L. Velasco-Ibarra, and F. Javier Pérez-Flores
for technical support.
Notes and references
1 For general reviews on allylic oxidation see:
(a) P. C. Bulman and T. J. McCarthy, in Comprehensive
Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford,
1991, vol. 7, pp. 83–117; (b) A. Nakamura and M. Nakada,
Synthesis, 2013, 45, 1421–1451; For recent reviews on allylic
oxidation with Cu see: (c) M. B. Andrus and J. C. Lashley,
Tetrahedron, 2002, 58, 854–866; (d) T. Punniyamurthy and
L. Rout, Coord. Chem. Rev., 2008, 252, 134–154. For recent
reviews on allylic oxidation with Pd see: (e) I. I. Moiseev
and M. N. Vargaftik, Coord. Chem. Rev., 2004, 248, 2381–
2391; (f) H. Grennberg and J.-E. Baeckvall, in Transition
Metals for Organic Synthesis, ed. M. Beller and C. Bolm,
Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2nd edn,
2004, ch. 2.3, vol. 2, pp. 243–255; For a recent review on
metal-free allylic oxidation see: K. Chen, P. Zhang, Y. Wang
and H. Li, Green Chem., 2014, 16, 2344–2374.
2 Selected examples of allylic oxidation with enzymes:
(a) M. A. Fraatz, S. J. L. Riemer, R. Stöber, R. Kaspera,
M. Nimtz, R. G. Berger and H. Zorn, J. Mol. Catal. B:
Enzym., 2009, 61, 202–207; (b) A. Rickert, V. Krombach,
O. Hamers, H. Zorn and W. Maison, Green Chem., 2012, 14,
639–644; (c) V. Weidmann, M. Schaffrath, H. Zorn,
J. Rehbein and W. Maison, Beilstein J. Org. Chem., 2013, 9,
7 R. Nolla-Saltiel, E. Robles-Marín and S. Porcel, Tetrahedron
Lett., 2014, 55, 4484–4488.
8 (a) C.-G. Yang, N. W. Reich, Z. Shi and C. He, Org. Lett.,
2005, 7, 4553–4556; (b) S. W. Youn and J. I. Eom, J. Org.
Chem., 2006, 71, 6705–6707; (c) Y. Ito, R. Kato,
K. Hamashima, Y. Kataoka, Y. Oe, T. Ohta and I. Furukawa,
J. Organomet. Chem., 2007, 692, 691–697.
9 Selected recent examples of the use of 4H-benzo[d][1,3]-
dioxin-4-ones in organic synthesis: (a) O. Soltani and
J. F. De Brabander, Angew. Chem., Int. Ed., 2005, 44, 1696–
1699; (b) J. García-Fortanet, J. R. Debergh and J. K. De
Brabander, Org. Lett., 2005, 7, 685–688; (c) S.-W. Kang,
C. M. Gothard, S. Maitra, A. Wahab and J. S. Nowick, J. Am.
Chem. Soc., 2007, 129, 1486–1487; (d) Y. Y. Durmaz,
V. Kumbaraci, A. L. Demirel, N. Talinli and Y. Yagci, Macro-
molecules, 2009, 42, 3743–3749; (e) T. Yoshino, I. Sato and
M. Hirama, Org. Lett., 2012, 14, 4290–4292; (f) H. Gündüz,
V. Kumbaraci and N. Talinli, Helv. Chim. Acta, 2014, 97,
1097–1105.
2233–2241. Selected examples of allylic oxidation with: 10 U. Ichiro, Y. Yori and N. Satoshi, JP 2010/009435A,
PhIO and PhIO2: U. Atmaca, H. K. Usanmaz and M. Celik, 2010.
Dalton Trans.
This journal is © The Royal Society of Chemistry 2015