In Situ Generation of Phosphoryl Alkylindiums and Their Synthetic Application to Arylalkyl Phosphonates via Palladium-Catalyzed Cross-Coupling Reactions

Phosphoryl alkylindium reagents are generated in situ from the direct insertion of indium with bromoalkyl phosphonates in the presence of CuCl, and their synthetic application to arylalkyl phosphonates is reported via a Pd-catalyzed cross-coupling reaction with tolerance of a diversity of functional groups including ester, ketone, aldehyde, nitrile, nitro, trifluoromethyl, chloride, methoxy, hydroxy, and amino

Synthesis of 2‑Alkoxyaryl-2-aryl Enamines via Tandem Copper-Catalyzed Cycloaddition and Rhodium-Catalyzed Alkoxyarylation from Alkynes, <i>N</i>‑Sulfonyl Azides, and Aryl Ethers

A synthetic route to a wide range of 2-alkoxyaryl-2-aryl enamines is developed from Rh-catalyzed alkoxyarylation of <i>N</i>-sulfonyl-4-aryl-1,2,3-triazoles with aryl ethers via the elimination of nitrogen molecule. In addition, 2-alkoxyaryl-2-aryl enamines are prepared via tandem Cu-catalyzed cycloaddition and Rh-catalyzed alkoxyarylation starting from alkynes, <i>N</i>-sulfonyl azides, and aryl ethers in one-pot

Alkenylation of Phosphacoumarins via Aerobic Oxidative Heck Reactions and Their Synthetic Application to Fluorescent Benzo­phospha­coumarins

Alkenylation of phosphacoumarins is developed from the reaction of phosphacoumarins with a variety of activated as well as nonactivated alkenes via aerobic oxidative Heck reactions. In addition, 3-alkenyl­phospha­coumarins undergo an inverse electron demand Diels–Alder reaction (IEDDA) with enamines <i>in situ</i> generated from ketone and pyrrolidine followed by 1,2-elimination and a dehydrogenation, producing fluorescent benzo­phospha­coumarins

ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2<i>H</i>‑hydronaphthalene and chromene) and 2<i>H</i>‑Quinoline Bearing an Alkenyl Iodide Moiety

Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis­(2<i>H</i>-hydronaphthalene and chromene) and 2<i>H</i>-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris­(arylthiolate) to produce the functionalized styrene derivatives