Eur. J. Org. Chem. 2016 · ISSN 1099–0682 SUPPORTING ...

Eur. J. Org. Chem. 2016 · ISSN 1099–0682 SUPPORTING INFORMATION DOI: 10.1002/ejoc.201600311 Title: Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium-Catalyzed Arylation Author(s): Ruth Dorel, Paula de Mendoza, Pilar Calleja, Sergio Pascual, Esther González-Cantalapiedra, Noemí Cabello, Antonio M. Echavarren*

Table of contents

1. 1H-NMR and 13C-NMR Spectra…………………………….………………..........S1 2. Crystal Data and Structure Refinement 3.1. anti-4b…………………………………………………………….....…..S6 3.2. 8…………………………………………………………………….…..S18

1. 1H-NMR and 13C-NMR Spectra 4,9,14-Tribromo-5,10,15-tris((1-bromonaphthalen-2-yl)methyl)-10,15-dihydro-5Hdiindeno[1,2-a:1',2'-c]fluorene (4a).

S1

(5R*,10S*,15S*)-5,10,15-tris((1-bromonaphthalen-2-yl)methyl)-4,9,14-trimethoxy-10,15dihydro-5H-diindeno[1,2-a:1',2'-c]fluorine (anti-4b).

S2

3,13,23-Trimethoxy-benzo[1,2-e:3,4-e’:5,6-e’’]tribenzo[l]acephenanthrylene (8).

S3

3,13,23-Trihydroxy-benzo[1,2-e:3,4-e’:5,6-e’’]tribenzo[l]acephenanthrylene (9).

S4

(5S,10S,15S)-2,7,12-Tribromo-5,10,15-tris((1-bromonaphthalen-2-yl)methyl)-10,15-dihydro5H-diindeno[1,2-a:1',2'-c]fluorene (syn-6).

S5

2. Crystal Data and Structure Refinement

Table S1. Crystal data and structure refinement for 4b. _____________________________________________________________________ Empirical formula

C64.50 H47.50 Br3 Cl3.50 O3

Formula weight

1234.33

Temperature

100(2) K

Wavelength

0.71073 Å

Crystal system

Triclinic

Space group

P-1

Unit cell dimensions

a = 8.0931(10)Å

= 96.447(7)°.

b = 17.827(2)Å

 = 101.203(5)°.

c = 18.954(3)Å

 = 95.038(6)°.

Volume

2648.6(6) Å3

Z

2

Density (calculated)

1.548 Mg/m3

Absorption coefficient

2.510 mm-1

F(000)

1246

Crystal size

0.20 x 0.04 x 0.02 mm3

Theta range for data collection

3.246 to 27.558°.

Index ranges

-10