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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information An Unprecedented Tandem Synthesis of Fluorescent Coumarin-Fused Pyrimidines via Copper-Catalyzed Cross-Dehydrogenative C(sp 3 ) Bond Coupling Santosh Kumari, [a] S. M. Abdul Shakoor, [a] Sadhika Khullar, [b] Sanjay K. Mandal, [c] and Rajeev Sakhuja* [a] [a] Department of Chemistry, Birla Institute of Technology & Science, Pilani, Rajasthan, , India [b] Department of Chemistry, D.A.V. University, Jalandhar-Pathankot ational Highway, Jalandhar , Punjab, India [c] Department of Chemical Sciences, Indian Institute of Science Education and Research Mohali, Sector 81, S.A.S. agar, Manuali P.., Punjab , India Fax: , Tel: sakhuja.rajeev@gmail.com Contents Page o H & C MR spectra of 3a-y, 3a & 3a D (CSY & HETCR) spectra of 3a 29 3z+3z 3. 1 H MR & Mass analysis of X-ray Crystallography Studies of 3a 31 1

2 . 1 H & C MR spectra of 3a-r, 3a & 3a 1 H MR of 3a C MR of 3a 2

3 H MR of 3b C MR of 3b 3

4 H MR of 3c C MR of 3c 4

5 H MR of 3d Me Me C MR of 3d Me Me 5

6 H MR of 3e Me Me C MR of 3e Me Me 6

7 H MR of 3f Me Me Me Me C MR of 3f Me Me Me Me 7

8 H MR of 3g C MR of 3g 8

9 H MR of 3h C MR of 3h 9

10 H MR of 3i C MR of 3i 10

11 H MR of 3j F F C MR of 3j F F 11

12 H MR of 3k C MR of 3k 12

13 H MR of 3l C MR of 3l

14 H MR of 3m Me Me C MR of 3m Me Me 14

15 H MR of 3n Me Me C MR of 3n Me Me 15

16 H MR of 3o Me Me Me Me C MR of 3o Me Me Me Me 16

17 H MR of 3p F F C MR of 3p F F 17

18 H MR of 3q Br C MR of 3q Br 18

19 H MR of 3r Br C MR of 3r Br 19

20 H MR of 3s Br Me Me C MR of 3s Br Me Me 20

21 H MR of 3t Br Me Me Me Me C MR of 3t Br Me Me Me Me 21

22 H MR of 3u Br C MR of 3u Br 22

23 H MR of 3v Br C MR of 3v Br 23

24 H MR of 3w C MR of 3w 24

25 H MR of 3y Br C MR of 3y Br 25

26 H MR of 3y C MR of 3y 26

27 H MR of 3a' (or A) H C MR of 3a' (or A) H 27

28 H MR of 3a'' (or B) H C MR of 3a'' (or B) H 28

29 2. 1 H & C MR spectra of 3a-r4. 2D (CSY & HETCR) spectra of 3a 29

30 3. Mass analysis of mixture of cross-coupled product (3z) and homo-coupled products (3a & 3d) using two different benzyl amines 1 3z+3z H MR and Mass analysis of + Me Me 30

31 4. X-ray Crystallography Studies of 3a Crystals of 3a were screened under a microscope for mounting in a nylon loop attached to a goniometer head. Initial crystal evaluation and data collection were performed on a Kappa APEX II diffractometer equipped with a CCD detector (with the crystal-to-detector distance fixed at 60 mm) and sealed-tube monochromated MoK radiation using the program APEX2. 1 By using the program SAIT 1 for the integration of the data, reflection profiles were fitted, and values of F 2 and (F 2 ) for each reflection were obtained. Data were also corrected for Lorentz and polarization effects. The subroutine XPREP 1 was used for the processing of data that included determination of space group, application of an absorption correction (SADABS) 1, merging of data, and generation of files necessary for solution and refinement. The crystal structure was solved and refined using SHELX In each case, the space group was chosen based on systematic absences and confirmed by the successful refinement of the structure. Positions of most of the non-hydrogen atoms were obtained from a direct methods solution. Several full-matrix least-squares/difference Fourier cycles were performed, locating the remainder of the non-hydrogen atoms. All non-hydrogen atoms were refined with anisotropic displacement parameters. All hydrogen atoms were placed in ideal positions and refined as riding atoms with individual isotropic displacement parameters. All figures were drawn using MERCURY V and Platon. 4 Crystal data for 3a. C 24 H , Mr = g/mol, monoclinic, space group C2/c, a = (4) Å, b = 9.871(2) Å, c = (4) Å, α = 90, β = (5), γ = 90, V = 3736(1) Å 3, Z = 8, T = 296(2) K, D calcd = g/cm 3 ; Full matrix least-square on F 2 ; R 1 = 0.046, wr 2 = for 2274 observed reflections [I > 2 (I)] and R 1 = 0.073, wr 2 = for all 3294 reflections; GF = CCDC o Fully labelled RTEP of 3a (R stereoisomer) is shown below: References 1. APEX2, SADABS and SAIT; Bruker AXS inc: Madison, WI, USA, Sheldrick, G. M. Acta Cryst. 2008, A64, Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edginton, P. R.; McCabe, P.; Pidocck, E.; Rodriguez-Monge, L.; Taylor, T.; Van de Streek, J.; Wood, P. A. J. Appl. Cryst.,2008, 41, Spek, A. L. PLAT, Version 1.62, University of Utrecht,