Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles

Abstract

Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 atm of carbon monoxide and at 110 degrees C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.

Cascade Palladium‐ and Copper‐Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors

“…Scheme 15. Although no reaction intermediates were detected, a brief mechanistic investigation suggested that the intramolecular amination preceded the intermolecular Suzuki coupling. Established Heck, [34] carbonylation [35] and Sonogashira [36] methodologies can be incorporated as tandem processes, resulting in 2-alkenyl-, 2-carboxy-and 2-alkenylindoles, respectively. The modular nature of the process was found to be particularly effective for such syntheses.…”

Palladium‐Catalyzed Domino Cyclization/Phosphorylation of gem‐Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics

“…In recent years, gem-dihaloolefins have been recognized as a type of useful starting material for the synthesis of functionalized heteroaromatics, meanwhile, diverse functional groups can be introduced in one step. [8][9][10][11][12] The groups of Lautens, [9] Wang, [10] Alper [11] and others [12] have realized transition-metal-catalyzed tandem cyclization/functionalization of gem-dihaloolefins with various nucleophiles, which afforded C2-halogenated, (hetero)aryled, alkenyled, alkynyled, cyanated, trifluoromethylthiolated(selenolated), and carbonylated benzofused heterocycles. In 2004, Bisseret and coworkers [8g] reported a palladium-assisted cyclization/ phosphorylation of gem-dibromoolefins with diethylphosphonate for synthesizing C2-phosphorylated benzofuran or indole.…”

Highly Efficient Microwave-Assisted CO Aminocarbonylation with a Recyclable Pd(II)/TPP-β-Cyclodextrin Cross-Linked Catalyst

“…The term 'carbonylation', coined by Reppe in the '30s, includes a plethora of reactions 1 such as formylation, 2 hydroformylation, alkoxycarbonylation, 3,4 aminocarbonylation, [5][6][7] carbonylative Heck, 8 carbonylative Suzuki Miyaura, 9 carbonylative Sonogashira reactions, [10][11] which provide an easy and practical method for the introduction of a carbonyl group into an organic substrate.…”