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1 Z. Anorg. Allg. Chem ISSN SUPPORTING INFORMATION Title: Lanthanides Mediated Oxidative Cross Coupling of Benzylalcohols and Various Amines to Form Corresponding Imines Author(s): J. Bhattacharjee, M. Sachdeva, T. K. Panda* Ref. No.: Z
2 Supporting Information for Lanthanides Mediated Oxidative Cross Coupling of Benzyl Alcohols and Various Amines to form corresponding Imines JAYEETA BHATTACHARJEE, MITALI SACHDEVA, TARUN K. PANDA* Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi , Sangareddy, Telangana, India. Table of Contents 1. Experimental Section 2. NMR data of compounds (A-N). 3. Spectroscopic data for imine derivatives.
3 1.1 General Information All manipulations of air-sensitive materials were performed under inert atmosphere and in flame-dried Schlenk-type glassware, either on a dual manifold Schlenk line interfaced with a high vacuum (10 4 Torr) line, or in an argon-filled MBRAUN glovebox. Hydrocarbon solvents (toluene and n-hexane) were distilled under nitrogen from LiAlH 4 and stored in the glove box. 1 H NMR (400 MHz) and 13 C{ 1 H} (100 MHz), spectra were recorded on a BRUKER AVANCE III-400 spectrometer. All amines, alcohol and catalyst were purchased from either Sigma Aldrich or Alfa Aesar. Amines were distilled over CaH 2 prior to use. 1 NMR solvent (CDCl 3 ) was purchased from Alfa Aesar and distilled over molecular sieves. General procedure for the cross coupling of alcohols and amines to form imines: A mixture of amine (1.5 mmol), alcohol (1 mmol), Ln-catalyst (5 mol % based on amine) and KOH (53 mg, 1.0 mmol) in toluene were placed in a 10 ml glass tube. Then, the reaction mixture was stirred under oxygen atmosphere at 90 C for 12 hours before it was quenched by NH 4 Cl (2 ml, sat. aq.). The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried using Na 2 SO 4 and concentrated in vacuo. The product was characterized by 1 H and 13 C NMR spectroscopy. The yield of product was analyzed using 1 H NMR spectroscopy and calculated with the help of isolated pure products. N-benzylidene-1-phenylmethanamine.[A] Yield: 195 mg, 99%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.30 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 4H, Ar), (m, 2H, Ar), 4.73 (s, 2H, CH 2 ). 13 C NMR (100 MHz, CDCl 3 ): δ = 160.7, 152.4, 136.6, 131.8, 129.5, 129.2, 126.3, N-Benzylideneaniline. [B]
4 Yield: 181 mg, 99%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.32 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 2H, Ar), (m, 3H, Ar). 13 C NMR (100 MHz, CDCl 3 ): δ = 159.4, 150.9, 135.1, 130.3, 128.2, 127.8, 117.4, 111.1, N-Benzylidine-2-fluoroaniline. [C] Yield: 182 mg, 96%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.33 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 4H, Ar), (m, 1H, Ar); 13 C NMR (100 MHz, CDCl 3 ): δ = 159.4, 150.9, 135.1, 128.8, 127.9, 124.8, 119.8, 117.4, 110.4, N-Benzylidene-2-chloroaniline. [D] Yield: 201 mg, 95%. 1 H NMR (400 MHz, CDCl 3 ): δ 8.41 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 2H, Ar), (m, 2H, Ar), (m, 2H, Ar); 13 C NMR (CDCl 3, 100 MHz): δ = 162.1, 149.6, 142.9, 135.8, 131.8, 129.8, 129.4, 128.8, 127.6, 120.1, 119.1, 115.9, N-Benzylidene-2-iodoaniline. [E] Yield: 290 mg, 91%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.33 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 4H, Ar), (m, 1H, Ar); 13 C NMR (100 MHz, CDCl 3 ): δ = 159.3, 150.9, 135.1, 130.3, 128.8, 128.1, 127.9, 126.4, 120.1, 119.0, 115.9, 77.5; ESI-HRMS (TOF) for [M-H (C13H9IN)]+: Calcd. m/z = , found N-Benzylidine-2-methylaniline. [F] Yield: 180 mg, 84%. 1 H NMR (400 MHz, CDCl 3 ) : δ = 8.23 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 1H, Ar), (m, 1H, Ar), (m, 2H, Ar), (m, 1H, Ar) 2.26 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) : δ = 159.6, 151.2, 144.5, 131.3, 130.7, 130.3, 129.0, 127.0, 125.7, 118.7, 117.8, 77.5, Benzylidine-3-methylaniline. [G] Yield: 195 mg, 99%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.33 (s, 1H, CH), (m, 2H, Ar), (m, 3H, 7Ar), 7.11 (m, 1H, Ar), 6.93 (m, 3H, Ar), 6.38 (m, 1H, Ar), 2.28 (s, 3H, CH 3 ); 13 C NMR (100 MHz, CDCl 3 ): δ = 159.5, , 144.6, 131.3, 128.8, 128.5, 127.0, 125.7, 118.7, 117.8, 115.1, 77.0, 17.9.
5 N-Benzylidine-4-methylaniline. [H] Yield: 180 mg, 84%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.45 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 2H, Ar), (m, 2H, Ar), (m, 1H, Ar), 2.38 (s, 3H, CH 3 ); 13 C NMR (100 MHz, CDCl 3 ): δ = 159.5, 151.2, 144.4, 131.3, 130.5, 128.6, 126.8, 125.7, 118.7, 117.6, 115.7, 77.5, N-Benzylidine-4-methoxy-2-methylaniline. [J] Yield: 225 mg, 99%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.48 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 1H, Ar), ,48 (m, 2H, Ar), 3.66 (s, 3H, OCH 3 ), 2.28 (s, 3H, CH 3 ); 13 C NMR (100 MHz, CDCl 3 ): δ = 158.6, 157.7, 152.8, 136.8, 130.9, 128.7, 118.2, 116.4, 115.9, , 56.7, N-benzylidenecyclohexanamine. [K] Yield: 180 mg, 95%. 1 H NMR (400 MHz, CDCl 3 ): δ 8.23 (s, 1H, CH) (m, 2H, Ar), (m, 3H, Ar), (m, 1H, Cy), (m, 8H, Cy), 1.16 (m, 3H, Cy); 13 C NMR (100 MHz, CDCl 3 ) : δ = 163.3, 136.4, 131.9, 129.9, 128.8, 128.5, 77.1, 25.7, 24.7, N-Benzylidine-2, 6-dimethylaniline.[M] Yield: 35 mg, 15%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.22 (s, 1H), (m, 2H), (m, 3H), (m, 3H), 2.16 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ): δ = 162.6, 151.2, 136.1, 131.5, 128.8, 128.6, 128.1, 127.2, 123.7, N-(4-methoxybenzylidene)-1-phenylmethanamine. [N] Yield: 101 mg, 45%. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.21 (s, 1H, CH), (m, 2H, Ar), (m, 3H, Ar), (m, 4H, Ar), 4.73 (s, 2H, CH 2 ), 3.69 (s, 3H, OCH 3 ) ; 13 C NMR (100 MHz, CDCl 3 ): δ = 158.6, 157.7, 152.8, 136.8, 130.9, 128.7, 118.2, 116.4, 115.9, , 56.7, 18.2.
6 Figure S1. 1 H NMR spectra of the reaction without catalyst. Figure S2. 1 H NMR spectra of compound A.
7 Figure S3. 13 C NMR spectra of compound A. Figure S4. 1 NMR spectra of compound B.
8 Figure S5. 13 C NMR spectra of compound B. Figure S6. 1 H NMR spectra of compound B.
9 Figure S7. 13 C NMR spectra of compound C. Figure S8. 1 H NMR spectra of compound D.
10 Figure S9. 13 C NMR spectra of compound D. Figure S10. 1 H NMR spectra of compound E.
11 Figure S C NMR spectra of compound E. Figure S12. 1 H NMR spectra of compound F.
12 Figure S C NMR spectra of compound F. Figure S14. 1 H NMR spectra of compound G.
13 Figure S C NMR spectra of compound G. Figure S16. 1 H NMR spectra of compound H.
14 Figure S C NMR spectra of compound H. Figure S18. 1 H NMR spectra of compound J.
15 Figure S C NMR spectra of compound J. Figure S20. 1 h NMR spectra of compound K.
16 Figure S21. 1 H NMR spectra of compound M.
17 Figure S22. 1 H NMR spectra of compound N. Figure S C NMR spectra of compound N. References. [1] L. Jiang, L. Jin, H. Tian, X. Yuan, X. Yu, Q. Xu. Chem. Commun. 2011, 47, [2] A. Kumar, A. G. Samuelson, J. Organomet. Chem. 2010, 695, 338. [3] I. Iovel, L. Golomba, M. Fleisher, J. Popelis, S. Grinberga, E. Lukevics, Chem. Heterocycl. Compd, 2004, 40, 701. [4] J. W. Sadownik, D. Philp, Angew. Chem. Int. Ed. 2008, 47, [5] T. Axenrod, X. H. Huang, M. J. Wieder, C. M. Watnick, Magn. Reson. Chem. 1986, 24, 274. [6] J. R. Wang, Y. Fu, B. B. Zhang, X. Cui, L. Liu, Q. X. Guo, Tetrahedron Lett. 2006, 47, [7] J. S. Bennett, K. L. Charles, M. R. Miner, C. F. Heuberger, E. J. Spina, M. F. Bartels, T. Foreman, Green Chem. 2009, 11, 166.
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