, s, 1H), 7.91 (s, 1H), 7.71 -7.67 (m, 1H)

, 4,4'-dimethyl-2,2'-bipyridine (25): Following the general procedure using 4,4'-dimethyl-2,2'-bipyridine (442 mg, 2.4 mmol) and 4-bromoaniline (103 mg

, the residue was purified by flash chromatography on silica gel (heptane-EtOAc, 98-2) to afford the desired compound 25 (98 mg, 48%). 1 H NMR (400 MHz

. Hz,

J. J. Douglas, M. J. Sevrin, C. R. Stephenson, M. H. Shaw, J. Twilton et al., Visible Light Photocatalysis: Applications and New Disconnections in the Synthesis of Pharmaceutical Agents, Org. Process Res. Dev, vol.20, pp.4505-4513, 2016.

S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-razzaq, H. Lee et al., Highly Phosphorescent Bis-Cyclometalated Iridium Complexes: Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes, J. Am. Chem. Soc, vol.123, pp.4304-4312, 2001.

T. Alves, A. B. De-oliveira, V. Snieckus, V. Bonnet, F. Mongin et al., Syntheses of Substituted Pyridines, Quinolines and Diazines via Palladium-Catalyzed Cross-Coupling of aryl Grignard Reagents, Tetrahedron Lett, vol.29, pp.4429-4438, 1988.

R. P. Volante, P. J. Reider, E. Negishi, T. Takahashi, and A. O. King, Synthesis of 5-Pyridyl-2-furaldehydes via Palladium-Catalyzed Cross-Coupling with Triorganozincates, Org. Synth, vol.4, pp.67-74, 1988.

S. Sibille, V. Ratovelomanana, J. Y. Nedelec, J. Perichon, W. Su et al., An Efficient Route to Unsymmetrical Biaryls via the Electrochemical Preparation of Functionalized Aromatic Zinc Organometallics, Synlett, pp.425-426, 1993.

;. Lett, C. Wolf, R. Lerebours, M. Beley, S. Chodorowski et al., Unusual C-6 Lithiation of 2-Chloropyridine-Mediated by BuLi-Me2N(CH2)2OLi. New Access to 6-Functional-2-chloropyridines and Chloro-bisheterocycles, Spiroquinazolinones as Novel, Potent, and Selective PDE7 Inhibitors, vol.6, pp.4623-4626, 1993.

M. J. Rashkin, M. L. Waters, A. J. Wilkinson, H. Puschmann, J. A. Howard et al., Unexpected Substituent Effects in Offset ?-? Stacked Interactions in Water, An Alternative Route to Highly Luminescent Platinum(II) Complexes: Cyclometalation with N-C-N-Coordinating Dipyridylbenzene Ligands, vol.124, pp.8609-8611, 2002.

K. Godula, B. Sezen, D. Sames, W. Hagui, N. Besbes et al., Direct access to 2-(hetero)arylated pyridines from 6-substituted 2-bromopyridines via phosphine-free palladium-catalyzed C-H bond arylations: the importance of the C6 substituent, Palladium Supported on Mesoporous Silica/Graphene Nanohybrid as a Highly Efficient and Reusable Heterogeneous Catalyst for C?H Functionalization, vol.127, pp.3487-3494, 2005.

F. Roudesly, L. F. Veiros, J. Oble, and G. Poli, Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N-Oxides, Org. Lett, vol.20, pp.2346-2350, 2018.

C. Wang, P. H. Dixneuf, and J. Soulé, Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds, Chem. Rev, vol.118, pp.7532-7585, 2018.

D. Xue, Z. Jia, C. Zhao, Y. Zhang, C. Wang et al., Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water, Chem. Eur. J, vol.20, pp.2960-2965, 2014.

J. Zhang, J. Chen, X. Zhang, X. Lei, F. Gomes et al., Total Syntheses of Menisporphine and Daurioxoisoporphine C Enabled by Photoredox-Catalyzed Direct C-H Arylation of Isoquinoline with Aryldiazonium Salt, Org. Chem. Front, vol.79, pp.464-469, 2014.

;. Commun, L. Buglioni, P. Riente, E. Palomares, M. A. Pericas et al., Visible-Light-Promoted Arylation Reactions Photocatalyzed by Bismuth(III) Oxide, Eur. J. Org. Chem, vol.52, pp.6986-6990, 2016.

. J. Eur, ;. Org, D. C. Fabry, Y. A. Ho, R. Zapf et al., Blue Light Mediated C-H Arylation of Heteroarenes using TiO2 as an Immobilized Photocatalyst in a Continuous-Flow Microreactor, Org. Biomol. Chem, vol.19, pp.289-299, 1911.

M. C. Fürst, E. Gans, M. J. Böck, and M. R. Heinrich, Visible-Light-Induced, Catalyst-Free Radical Arylations of Arenes and Heteroarenes with Aryldiazonium Salts, Chem. Eur. J, vol.23, pp.15312-15315, 2017.

C. G. Lima, M. De, T. Lima, M. Duarte, I. D. Jurberg et al., Organic Synthesis Enabled by Light-Irradiation of EDA Complexes: Theoretical Background and Synthetic Applications, ACS Catal, vol.6, pp.1389-1407, 2016.

F. P. Crisóstomo, T. Martín, and R. Carrillo, Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ, Angew. Chem. Int. Ed, vol.53, pp.2181-2185, 2014.

D. M. Monzón, T. Santos, F. Pinacho-crisóstomo, V. S. Martín, and R. Carrillo, Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines, Chem. Asian J, vol.13, pp.325-333, 2018.

D. Hata, T. Moriuchi, T. Hirao, and T. Amaya, Polyaniline-Induced Arylation with Arenediazonium Salts Derived from Anilines, Chem. Eur. J, vol.23, pp.7703-7709, 2017.

A. P. Colleville, R. A. Horan, S. Olazabal, and N. C. Tomkinson, C-H Arylation of Heterocyclic N-Oxides Through in Situ Diazotisation Of Anilines without Added Promoters: A Green And Selective Coupling Process, Org. Process Res. Dev, vol.20, pp.1283-1296, 2016.

D. Cantillo, C. Mateos, J. A. Rincon, O. De-frutos, and C. O. Kappe, Light-Induced C-H Arylation of (Hetero)arenes by In Situ Generated Diazo Anhydrides, Chem. Eur. J, vol.21, pp.12894-12898, 2015.

J. Tauber, D. Imbri, and T. Opatz, Radical Addition to Iminium Ions and Cationic Heterocycles, Molecules, vol.19, pp.16190-16222, 2014.

R. S. Proctor, R. J. Phipps, V. Viton, V. Desvergnes, J. J. Jodry et al., Chiral Spiro Cu(I) Complexes. Supramolecular Stereocontrol and Isomerization Dynamics by the Use of TRISPHAT Anions, Angew. Chem. Int. Ed, vol.58, pp.2058-2065, 2006.

C. Zou, J. Lin, S. Suo, M. Xie, X. Chang et al., Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C?H Bond Arylation of Electron-Deficient Heteroaromatic Compounds, J. Am. Chem. Soc, vol.54, pp.1616-1620, 2009.

I. A. Mkhalid, D. N. Coventry, D. Albesa-jove, A. S. Batsanov, J. A. Howard et al., Ir-Catalyzed Borylation of C-H Bonds in N-Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters, Angew. Chem. Int. Ed, vol.45, pp.489-491, 2006.

D. Felipe-blanco, F. Alonso, and J. C. Gonzalez-gomez, Salicylic Acid-Catalyzed One-Pot Hydrodeamination of Aromatic Amines by tert-Butyl Nitrite in Tetrahydrofuran, Adv. Synth. Catal, vol.359, pp.2857-2863, 2017.

E. M. Simmons, J. F. Hartwig, H. Cano-yelo, A. Deronzier, H. Cano-yelo et al., On the Interpretation of Deuterium Kinetic Isotope Effects in C-H Bond Functionalizations by Transition-Metal Complexes, J. Chem. Soc., Perkin Trans, vol.51, pp.315-321, 1984.

Y. Li, W. Liu, and C. Kuang, Direct Arylation of Pyridines without the Use of a Transition Metal Catalyst, Chem. Commun, vol.50, pp.7124-7127, 2014.

A. Srinivasulu, B. Shantharjun, D. Vani, K. C. Ashalu, and A. Mohd,

J. Delord, F. Colobert, and K. R. Reddy, Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP, Eur. J. Org. Chem, pp.1815-1819, 2019.
URL : https://hal.archives-ouvertes.fr/hal-02161629

D. Prajapati, C. Schulzke, M. K. Kindermann, and A. R. Kapdi, Selective Palladium-Catalysed Arylation of 2,6-Dibromopyridine using N-Heterocyclic Carbene Ligands, RSC Advances, vol.5, pp.53073-53085, 2015.

J. Sim, M. Viji, J. Rhee, H. Jo, S. J. Cho et al., ?-Functionalization of ?,?-Unsaturated Nitriles under Mild Conditions: Versatile Synthesis of 4-Aryl-2-Bromopyridines, Adv. Synth. Catal, vol.361, pp.5458-5465, 2019.

M. L. Rao and R. J. Dhanorkar, Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines, Eur. J. Org. Chem, pp.5214-5228, 2014.