Synthesis of Alkyl Alkynyl Ketones by Pd/Light-Induced Three-Component Coupling Reactions of Iodoalkanes, CO, and 1-Alkynes

Abstract

Under photoirradiation conditions using xenon light, in the presence of a catalytic amount of PdCl(2)(PPh(3))(2) with triethylamine as a base, a three-component coupling reaction of iodoalkanes, carbon monoxide, and terminal alkynes proceeded to give alkyl alkynyl ketones in good yields.

Fast and Efficient Continuous Flow Method for the Synthesis of Ynones and Pyrazoles

“…1‐Phenylundec‐1‐yn‐3‐one (3l): 1 H‐NMR (400 MHz, CDCl 3 ): δ = 7.58–7.55 (m, 2H), 7.46–7.35 (m,3H), 2.65 (t, J = 7.6 Hz, 2H), 1.77–1.70 (m, 2H), 1.31–1.22 (m, 10H), 0.87 (t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ = 188.4, 133.0, 130.7, 128.6, 120.1, 90.6, 87.9, 45.6, 31.8, 29.3, 29.1, 29.0, 24.2, 22.7, 14.1.…”

“…(3g): [31] 1 H-NMR (400 MHz, CDCl 3 ): δ = 7.65-7.59 (m, 3H), 7.45-7.34 (m, 4H), 6.57 (dd, J =3.6, 1.6 Hz 1H). 13 [33] [34] [35] Phenyldodec-1-yn-3-one(3m): [ [30] The solution was passed throw preheating unit R3 (Φ = 1.0 mm, L = 500 cm, 2514 μL) at 70°C. After a steady state was reached (after 1 min), the final product solution was collected for 60 seconds.…”

Palladium‐Catalyzed Carbonylative Multicomponent Reactions

“…Ryu and co‐workeres developed a strategy combining radical carbonylation and acyl‐Pd‐catalyzed intermediary carbonylation. Utilizing this radical/metal hybrid strategy, the double carbonylative cyclization of 4‐alkenyl iodides separately with phenylacetylene, phenylboronic acid and alcohols was achieved (Scheme a). When the alcohol was replaced by diethylamine under higher CO pressure, even triple carbonylative products, α‐ketoamides, could be obtained (Scheme b) …”

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.…”