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ChemComm
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COMMUNICATION
Journal Name
DOI: 10.1039/C9CC00492K
Am. Chem. Soc. 2018, 140, 13580.
6
7
For selected reviews on decarboxylative strategies, see: (a)
N.Rodriguez, L.J. Gooßen, Chem.Soc.Rev. 2011, 40, 5030.(b) W.
Dzik, P. Lange and L. Gooßen, Chem. Sci. 2012, 3, 2671. (c) Y. Wei,
P. Hu, M. Zhang and W. Su, Chem. Rev.2017, 117, 8864.
For selected articles on photocatalyzed decarboxylation, see: (a) Z.
Zuo, D.W.C.MacMillan, J. Am. Chem. Soc. 2014, 136, 5257. (b) Z.
Zuo, D. T. Ahneman, L. Chu, J. A. Terrett, A. G. Doyle, D.W.C.
MacMillan, Science 2014, 345, 437(c) J. Xuan, Z.-G. Zhang, W.-J.
Xiao, Angew. Chem. Int. Ed. 2015, 54, 15632; Angew. Chem. 2015
,
127, 15854. (d) C. P. Johnston, R. T. Smith, S. Allmendinger, D.W.C.
MacMillan, Nature 2016, 536, 322. (e) H. Huang, K. Jia and Y. Chen,
ACS Catal. 2016, 6, 4983. (f) J. Lin, Z. Li, W. Su and Y. Li, Nat.
Comm. 2017, 8, 14353. (g) B. Yang, D. Yu, X.-X. Xu and F.-L. Qing,
ACS Catal. 2018, 8, 2839.
Scheme
6
.
Proposed mechanism for the decarboxylative
8
9
(a) Hydrazine and its Derivatives, In Kirk-Othmer - Encylopedia
Chemical Technology, 4th ed., Vol. 13; Kirk, R. E.; Othmer, D. F.,
Eds.; Wiley: New York, 1995.(b) U. Ragnarsson, Chem. Soc.
Rev.2001, 30, 205.
hydrazination.
We Thank European Research Council (ERC) under the
European Union’s Horizon 2020 research and innovation
programme (grant agreement No. 741623) for financial
support and P.B. thanks the Elitenetzwerk Bayern (SynCat) for
financial support. We also thank Dr.G. Huff for the in-situ IR
spectroscopy and N. Wurzer for an optical rotation
measurement.
Selected publications: (a) M. W.Panas, Z. Xie, H.N.Panas,
M.C.Hoener,
E.J.Vallender
and
G.M.Miller,
J.
NeuroimmunePharmacol.2012, 7, 866. (b) A.N. Araujo, F. Carvalho,
Md. L. Bastos, P.G. de Pinho, M.Carvalho, Arch. Toxicol. 2015, 89,
1151. (c) R.R. Gainetdinov, M. C. Hoener, M. D. Berry, Pharmacol.
Rev. 2018, 70, 549.
10 Gardner, T. S.; Rutherford Lee, J.; Fells, E.; Wenis, E. US Patent
US2908688, 1959; Chem. Abstr. 1962, 56, 25114.
Conflicts of interest
11 M.B.H. Youdim, D. Edmondson and K.F. Topton, Nat. Rev.
Neurosci. 2006, 7, 295.
There are no conflicts to declare
Notes and references
12 (a) G. Bold, A. Fassler, H.-G. Capraro, R. Cozens, T. Klimkait, J.
Lazdins, J. Mestan, B. Poncioni, J. Rosel, D. Stover, M. Tintelnot-
Blomley, F. Acemoglu, K. Ucci-Stoll, D. Wyss, M. Lang, J. Med.
Chem. 1988, 41, 3387. (b) K. F. Kroom, S. Dhillon, S.J. Keam, Drugs
2009, 69, 1107.
1. For selected reviews on photoredox catalysis, see: (a) L. Marzo, S.
K. Pagire, O. Reiser, B. König, Angew. Chem. Int. Ed. 2018 ,57,
10034; Angew. Chem. 2018, 130, 10188. (b) M. Kärkäs, J. Porco Jr. 13 (a) E. Mutschler, G. Geisslinger, H.K. Kroemer, P. Ruth and M.
and C. Stephenson, Chem. Rev. 2016, 116, 9683. (c) Nathan A.
Romero D. A. Nicewicz, Chem. Rev. 2016, 116, 10075. (d) K. Skubi,
T. Blum and T. Yoon, Chem. Rev .2016, 116, 10035. (e) M. H. Shaw,
J. Twilton, D. W. C. MacMillan, J. Org. Chem. 2016, 81, 6898. (f) J.
Schäfer-Korting, Drug Effects Textbook of Pharmacology and
Toxicology . 9th edition. Scientific publishing house, Stuttgart 2008
ISBN 978-3-8047-1952-1. (b) A. Barbeau, M. Roy, Neurology 1976
26, 399.
,
,
Twilton, C. C. Le, P. Zhang, M. H. Shaw, R. W. Evans, D.W.C. 14 Y. Miyake, K. Nakajima and Y. Nishibayashi, Chem. Eur. J. 2012, 18,
MacMillan Nat. Rev. Chem. 2017, 1, 52. 16473.
2. For selected examples, see: (a) A. Musacchio, L. Nguyen, G. Beard 15 M.-J. Zhang, G. M. Schroeder, Y.-H. He, Z. Guan, RSC Adv. 2016, 6,
and R. Knowles, J. Am. Chem. Soc. 2014, 136, 12217. (b) Z. Zuo, D. 96693.
Ahneman, L. Chu, J. Terrett, A. Doyle, D.W.C. MacMillan, Science 16 S. B. Lang, K. C. Cartwright, R. S. Welter, T. M. Locascio, J. A. Tunge,
2014, 345, 437. (c) J. Jeffrey, J. Terrett and D.W.C. MacMillan, Eur. J. Org. Chem. 2016, 3331.
Science 2015, 349, 1532 (d) J. Chu and T. Rovis, Nature 2016, 539, 17 The corresponding iPr-carbamates, derived from amines, are
272.
usually deprotected under harsh conditions, for instance: (a) HCl,
AcOEt, 100 ºC; (b) AlCl3, DCM; (c) HBr, H2O, reflux; (d) HCl, water,
90ºC, 48h.
3
4
M. Neumann, S. Füldner, B. Koenig and K. Zeitler, Angew.
Chem.Int. Ed. 2011, 50, 951; Angew. Chem.2011, 123, 981.
(a) Balzani, V.; Ceroni, P.; Juris, A., Photochemistry and 18 DEAD and DIAD performed equally well, but DBAD was chosen for
photophysics: concepts, research, applications; John Wiley & the versatility of the products.
Sons,2014. (b) E. Natarajan, P. Natarajan, Inorg. Chem, 1992, 31, 19 The lower yield was possibly due to the reduced solubility in
1215. (c) A.Vogler and H.Kunkely, Inorg. Chim. Acta, 2006, 359,
4130.
organic solvents.
20 R.A. Sheldon, J.K. Kochi, J. Am. Chem. Soc. 1968, 90 (24), 6688.
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(a) A. Hu, J.-J. Guo, H. Pan, H. Tang, Z. Gao, Z. Zuo, J. Am. Chem.
Soc. 2018, 140, 1612. (b) A. Hu, J.-J. Guo, H. Pan, Z. Zuo, Science
4 | J. Name., 2012, 00, 1-3
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