Fig. 2 Three-step organic synthesis of the carboncone[1,2] derivatives 1 from corannulene 2. Three-step organic synthesis of the carboncone[1,2] derivatives.

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Fig. 2 Three-step organic synthesis of the carboncone[1,2] derivatives 1 from corannulene 2. Three-step organic synthesis of the carboncone[1,2] derivatives 1 from corannulene 2. Conditions: (i.) (Ir(OMe)cod)2 [20 mole percent (mol %)], B2(pin)2 (6.5 equiv.), 4,4′-dimetylpyridine (40 mol %), sodium methoxide (10 mol %), cyclohexane, 85°C, 4 days; (ii.) 1-bromonaphthalene or 1-bromo-4-mesitylnaphthalene (10 equiv.), Pd(PPh3)4 (25 mol %), Cs2CO3 (30 equiv.), toluene/H2O (2:1), 100°C, 24 hours; (iii.) DDQ (20 equiv.), TfOH/CH2Cl2 (1:20), 10 min. cod, 1,5-cyclooctadiene; pin, pinacolato; cat., catalyst; DDQ, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Zheng-Zhong Zhu et al. Sci Adv 2019;5:eaaw0982 Copyright © 2019 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).