[1] (a) F. Fleming, Nitrile-containing natural products, Nat. Prod. Rep, 16 (1999) 597-606; (b) F.F. Fleming, L. Yao, P. Ravikumar, L. Funk, B.C. Shook, Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore, J. Med. Chem., 53 (2010) 7902-7917; (c) A. Kleemann, Pharmaceutical substances: Syntheses, Patents, Applications, 4th ed.; Thieme: Stuttgart, 2001.
[2] (a) J. Wang, F. Xu, T. Cai, Q. Shen, Addition of amines to nitriles catalyzed by ytterbium amides: An efficient one-step synthesis of monosubstituted N-arylamidines, Org. Lett., 10 (2008) 445-448; (b) T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V.V. Fokin, Rhodium-catalyzed transannulation of 1, 2, 3-triazoles with nitriles, J. Am. Chem. Soc., 130 (2008) 14972-14974; (c) S. Lu, J. Wang, X. Cao, X. Li, H. Gu, Selective synthesis of secondary amines from nitriles using Pt nanowires as a catalyst, Commun. Chem., 50 (2014) 3512-3515; (d) X. Wang, Y. Huang, Y. Xu, X. Tang, W. Wu, H. Jiang, Palladium-catalyzed denitrogenative synthesis of aryl ketones from arylhydrazines and nitriles using O2 as sole oxidant, J. Org. Chem., 82 (2017) 2211-2218.
[3] U. Dutta, D.W. Lupton, D. Maiti, Aryl nitriles from alkynes using tert-butyl nitrite: Metal-free approach to C-C bond cleavage, Org. Lett., 18 (2016) 860-863.
[4] (a) T. Cheng, Review of novel energetic polymers and binders–high energy propellant ingredients for the new space race, Des. Monomers Polym., 22 (2019) 54-65; (b) W.R. Martin, D.W. Ball, Small organic azides as high energy materials: Perazidoacetylene,‐ethylene, and‐allene, ChemistrySelect, 3 (2018) 7222-7225.
[5] (a) T.-S. Lin, W.H. Prusoff, Synthesis and biological activity of several amino analogs of thymidine, J. Med. Chem., 21 (1978) 109-112; (b) D.B. Smith, G. Kalayanov, C. Sund, A. Winqvist, T. Maltseva, V.J.-P. Leveque, S. Rajyaguru, S.L. Pogam, I. Najera, K. Benkestock, The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4′-azidocytidine against hepatitis C virus replication: the discovery of 4′-azido-2′-deoxy-2′-fluorocytidine and 4′-azido-2′-dideoxy-2′, 2′-difluorocytidine, J. Med. Chem., 52 (2009) 2971-2978; (c) J.A. Raeburn, J.D. Devine, Pharmacological findings during azidocillin treatment of chest infections, Scand. J. Infect. Dis., 5 (1973) 135-139; (d) P.P. Geurink, W.A. van der Linden, A.C. Mirabella, N. Gallastegui, G. de Bruin, A.E. Blom, M.J. Voges, E.D. Mock, B.I. Florea, G.A. van der Marel, Incorporation of non-natural amino acids improves cell permeability and potency of specific inhibitors of proteasome trypsin-like sites, J. Med. Chem., 56 (2013) 1262-1275.
[6] (a) N. Rodriguez, L.J. Goossen, Decarboxylative coupling reactions: a modern strategy for C–C-bond formation, Chem. Soc. Rev., 40 (2011) 5030-5048; (b) J. Schwarz, B. König, Decarboxylative reactions with and without light–a comparison, Green Chem., 20 (2018) 323-361.
[7] R. Shang, Transition metal-catalyzed decarboxylation and decarboxylative cross-couplings, in: New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation, Springer, 2017, pp. 3-47.
[8] (a) S. Arshadi, S. Ebrahimiasl, A. Hosseinian, A. Monfared, E. Vessally, Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N–H compounds, RSC Adv., 9 (2019) 8964-8976; (b) A. Monfared, S. Ebrahimiasl, M. Babazadeh, S. Arshadi, E. Vessally, Recent advances in decarboxylative trifluoromethyl (thiol) ation of carboxylic acids, J. Fluor. Chem., 220 (2019) 24-34; (c) A. Hosseinian, F.A.H. Nasab, S. Ahmadi, Z. Rahmani, E. Vessally, Decarboxylative cross-coupling reactions for P(O)–C bond formation, RSC Adv., 8 (2018) 26383-26398; (d) A. Hosseinian, P.D.K. Nezhad, S. Ahmadi, Z. Rahmani, A. Monfared, A walk around the decarboxylative C–S cross-coupling reactions, J. Sulfur Chem., 40 (2019) 88-112.
[9] D.A. Klein, Nitrile synthesis via the acid-nitrile exchange reaction, J. Org. Chem., 36 (1971) 3050-3051.
[10] D. Cantillo, C.O. Kappe, Direct preparation of nitriles from carboxylic acids in continuous flow, J. Org. Chem., 78 (2013) 10567-10571.
[11] D. Cartigny, A. Dos Santos, L. El Kaim, L. Grimaud, R. Jacquot, P. Marion, Nitrile synthesis through catalyzed cascades involving acid–nitrile exchange, Synthesis, 46 (2014) 1802-1806.
[12] D.H. Barton, J.C. Jaszberenyi, E.A. Theodorakis, The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates, Tetrahedron, 48 (1992) 2613-2626.
[13] F. Le Vaillant, M.D. Wodrich, J. Waser, Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation, Chem. Sci., 8 (2017) 1790-1800.
[14] F.L. Vaillant, J. Waser, Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents, Chimia, 71 (2017) 226-230.
[15] N.P. Ramirez, B. König, J.C. Gonzalez-Gomez, Decarboxylative cyanation of aliphatic carboxylic acids via visible-light flavin photocatalysis, Org. Lett., 21 (2019) 1368-1373.
[16] K. Ouchaou, D. Georgin, F. Taran, Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction, Synlett, (2010) 2083-2086.
[17] O. Loreau, D. Georgin, F. Taran, D. Audisio, Palladium‐catalyzed decarboxylative cyanation of aromatic carboxylic acids using [13C] and [14C]‐KCN, J. Label. Compd. Radiopharm., 58 (2015) 425-428.
[18] Z. Fu, Z. Li, Y. Song, R. Yang, Y. Liu, H. Cai, Decarboxylative halogenation and cyanation of electron-deficient aryl carboxylic acids via cu mediator as well as electron-rich ones through pd catalyst under aerobic conditions, J. Org. Chem., 81 (2016) 2794-2803.
[19] Z. Fu, L. Jiang, Z. Li, Y. Jiang, H. Cai, Ag/Cu-mediated decarboxylative cyanation of aryl carboxylic acids with K4Fe (CN) 6 under aerobic conditions, Synth. Commun., 49 (2019) 917-924.
[20] F. Song, R. Salter, L. Chen, Development of decarboxylative cyanation Reactions for C-13/C-14 carboxylic acid labeling using an electrophilic cyanating reagent, J. Org. Chem., 82 (2017) 3530-3537.
[21] E. Nyfeler, P. Renaud, Decarboxylative radical azidation using MPDOC and MMDOC esters, Org. Lett., 10 (2008) 985-988.
[22] C. Liu, X. Wang, Z. Li, L. Cui, C. Li, Silver-catalyzed decarboxylative radical azidation of aliphatic carboxylic acids in aqueous solution, J. Am. Chem. Soc., 137 (2015) 9820-9823.
[23] Y. Zhu, X. Li, X. Wang, X. Huang, T. Shen, Y. Zhang, X. Sun, M. Zou, S. Song, N. Jiao, Silver-catalyzed decarboxylative azidation of aliphatic carboxylic acids, Org. Lett., 17 (2015) 4702-4705.
[24] Z.C. Kennedy, C.A. Barrett, M.G. Warner, Direct functionalization of an acid-terminated nanodiamond with azide: enabling access to 4-substituted-1, 2, 3-triazole-functionalized particles, Langmuir, 33 (2017) 2790-2798.
[25] D.C. Marcote, R. Street-Jeakings, E. Dauncey, J.J. Douglas, A. Ruffoni, D. Leonori, Photoinduced decarboxylative azidation of cyclic amino acids, Org. Biomol. Chem., 17 (2019) 1839-1842.
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