Palladium Catalyzed Dicarbonylation of α-Iodo-Substituted Alkylidenecyclopropanes: Synthesis of Carbamoyl Substituted Indenones

Abstract

A palladium catalyzed dicarbonylation of α-iodo-substituted ACPs for the synthesis of carbamoyl substituted indenones has been developed. Two carbonyl groups were incorporated into the product with the cleavage of the proximal C−C bond of the ACPs. A broad range of carbamoyl substituted indenones were efficiently prepared in good to excellent yields.

Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.42−7.39 (m, 2H), 7.35 (dd, J = 10.4, 4.9 Hz, 2H), 7.30−7.25 (m, 3H), 6.89−6.85 (m, 2H), 6.73 (s, 1H), 3.87−3.80 (m, 4H), 3.73 (dd, J = 12.4, 8.1 Hz, 3H), 3.64−3.49 (m, 4H). 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) δ: 203. 8, 165.1, 159.7, 132.3, 129.1, 128.7, 128.2, 126.5, 124.7, 114.6, 107.5, 100.4, 67.1, 67.0, 55.5, 47.81, 42.5 1one (3ba).…”

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.5 Hz, 2H), 7.38−7.32 (m, 3H), 7.27 (d, J = 7.8 Hz, 1H), 7.25−7.22 (m, 1H), 7.10 (s, 1H), 6.91 (t, J = 7.2 Hz, 2H), 3.84 (d, J = 11.5 Hz, 4H), 3.73 (dt, J = 13.8, 9.2 Hz, 3H), 3.65−3.48 (m, 4H). 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) δ: 205. 1, 165.1, 156.6, 132.6, 129.4, 129.0, 128.9, 127.9, 126.6, 121.1, 121.0, 111.2, 106.4, 95.2, 67.1, 67.0, 55.7, 47.7, 42.5…”

Pd/Cu catalyzed carbonylation of α-aminoaryl-tethered alkylidenecyclopropanes: synthesis of furoquinoline derivatives

“…Recently, we have reported a palladium catalyzed dicarbonylation of α-iodo-substituted ACPs for the synthesis of carbamoyl substituted indenones (Scheme 1c). 15 With the continuous interest in the carbonylation reaction for the synthesis of a heterocyclic skeleton, 16 we assume that the oxidative carbonylation of α-aminoaryl-tethered ACPs 17 would provide an efficient procedure for the synthesis of furoquinolines. Herein, we report a palladium and copper co-catalyzed carbonylation of α-aminoaryl-tethered ACPs for the synthesis of furoquinoline derivatives (Scheme 1d).…”

Ruthenium-Catalyzed Carbonylation of α-Aminoaryl-Tethered Alkylidenecyclopropanes: Synthesis of Eight-Membered Benzolactams

“…Recently, we had developed a Pd/Cu-cocatalyzed carbonylation of α-aminoaryl-tethered ACPs, which provided furoquinoline derivatives via a carbonylation/cyclization process (Scheme a) . With a continuous interest in carbonylation of ACPs, we herein report a ruthenium-catalyzed carbonylation of α-aminoaryl-tethered ACPs for the synthesis of eight-membered benzolactams (Scheme b). In this transformation, the amino group served a dual role of both directing group and nucleophile to facilitate the metallacycle formation and the carbonylation.…”