Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral ald...

A Fe(acac)3-catalyzed decarboxylative coupling of 2-(aryl)vinyl carboxylic acids with cycloalkanes was developed by using DTBP as an oxidant through a radical process. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields (71-95%). The reaction also shows excellent stereoselectivity, and only trans-isomers are obtained.

The enantioselective conjugate addition reaction of 3-aryl-substituted oxindoles with methyl vinyl ketone promoted by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at the C3-position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 91% ee).

1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH(2)Cl(2). This methodology was utilized to synthesize 2-benzoyl quinolines.

Electron-rich aryl ethers and phenols react with isoprene (2-methylbuta-1,3-diene) in the presence of catalytic Bi(OTf)(3) at 40 °C to afford the corresponding prenylated or 2,2-dimethylchroman products, respectively, in moderate to good yields. This transformation offers a convenient and expedient entry to prenylated derivatives of electron-rich aromatics that often display enhanced biological...

A series of (E)-1-aryloxy-1-en-3-ynes has been prepared by Sonogashira coupling of 2-bromo-3-aryloxypropenoates with terminal alkynes using Pd(PPh(3))(4) and CuI as the catalysts in Et(3)N. The resulting enynyl-aryl ethers are found to be highly applicable to the synthesis of 2,4-disubstituted furans with an ester group at C-4 position through an Au/Ag-catalyzed annulation reaction under extrem...

A new NIR fluorescent probe, NIR-Pd, for palladium species was designed and synthesized, based on a HD NIR fluorophore and deprotection of aryl propargyl ethers by palladium. The probe NIR-Pd displayed either a large NIR fluorescence turn-on or ratiometric response to palladium with high sensitivity and selectivity. Additionally, the novel NIR probe can monitor palladium species in live HeLa ce...

Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes and alkynes affording only the 6-endo dig cyclization product. Additionally, a sequential indium-catalyzed IMHA and palladium-catalyzed Sonog...

Microwave-assisted unimolecular isomerization-Claisen domino reactions of 1,3-di(hetero)aryl propargyl trityl ethers lead, depending on the basicity of the amine, either to the formation of tricyclo[3.2.1.0(2,7)]oct-3-enes (with triethylamine) or to indanes (with DBU). Based upon product analyses and computations, this base dependent dichotomy can be rationalized as a sequel of pericyclic react...