The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source

Abstract

The palladium-catalyzed C3-cyanation of indoles via direct C–H functionalization was achieved utilizing CH3CN as the cyanide source through transition-metal-catalyzed C–CN bond cleavage.

Transition-Metal-Free and Base-Promoted Carbon–Heteroatom Bond Formation via C–N Cleavage of Benzyl Ammonium Salts

“…13 C { 1 H} NMR (100 MHz, CDCl 3 ): δ 137.7, 136.3, 130.5, 128.9, 128.3, 128.0, 126.6, 126.5, 124.5, 120.7, 110.5, 102.7, 102.5, 50.3. This compound is known …”

“…The title compound was prepared according to the general experimental procedure I, purified by column chromatography on silica gel, and eluted with PE/EA = 1:1 (v/v) to afford a white solid in 71% yield (45.0 mg). 1 38.4 (d, J C−P = 63.9 Hz). 31 P { 1 H} NMR (162 MHz, CDCl 3 ): δ 28.9.…”

“…This compound is known. 38 10-Benzyl-10H-phenothiazine (7d). The title compound was prepared according to the general experimental procedure II, purified by column chromatography on silica gel, and eluted with PE/EA = 50:1 (v/v) to afford a pale yellow solid in 59% yield (34.1 mg).…”

Cobalt-Catalyzed Deacylative Ipso-C–C Bond Functionalization: An Approach toward Indole-Acyloins and Its Photophysical Studies

“…We presume that both 3-pivaloylindole and aryl 1,2-diketone coordinate with the metal catalyst to drive this unusual C3–C bond cleavage and functionalization process. Notably, all the prior metal-catalyzed indole C 3 -functionalizations were achieved through C3–H bond cleavage and not through ipso -C3–C bond cleavage (Figure b). , However, we achieved the cobalt­(III)-catalyzed deacylative C3–C bond ( ipso -) functionalization of indole (Figure c). Many challenges were overcome in this method such as the use of unexplored 1,2-diketones as a reacting partner.…”