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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 388. Synthesis and Oxidation of [n]Cyclo-1,8-carbazolylenes.

Scheme 388

Reagents and conditions: (a)759 slow addition of 388.2 over 1 h to Ni(cod)2 (250 mol %), cod (250 mol %), 2,2′-bipyridyl (150 mol %), THF, 80 °C, then, 80 °C, 1 h; (b) n-BuLi, toluene, −80 °C, then 0 °C, 30 min, (2) BBr3, −80 °C, then rt, 3 h; (c) PhSiCl3, Et3N, 1,2-DCE, 90 °C, 12 h; (d) PCl3, Et3N, 1,2-DCE, 90 °C, 16 h; (e) m-CPBA, DCM, 30 min; (f)760 DDQ (1.5 equiv), CHCl3 stabilized by 0.3–1.0% EtOH, rt; (g) DDQ (2.0 equiv), EtOH-free CHCl3, rt, 95%.