Analytical Methods in Oceanography by Gould R.F. (ed.)

By Gould R.F. (ed.)

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The resulting mixture was extracted with ethyl acetate (15 mL × 3), and the combined extract was dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give the desired dihaloalkenes. Due to the unique physical and biological properties of fluorinated molecules, the corresponding vinyl fluoride products were quite attractive for synthetic and medicinal chemists [145–149]. Although the halide nucleoaddition to haloalkynes have provided a diverse set of haloalkene derivatives, the incorporation of fluorine atom into the final olefin products through transition metal catalysis is still a challenging target.

42). Later, Jiang’s group [172] documented the nucleophilic addition of isocyanides to bromoalkynes via palladium catalysis, and Vadola [173] realized the gold-catalyzed dearomative spirocyclization of aryl alkynoate esters. General Procedure Indium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes: A mixture of 1,3-dicarbonyl compound (2 mmol), 1-iodoalkyne (3 mmol), and In(NTf2)3 (5 mol%) in toluene (2 mL) was heated in the dark at 70 °C for 4 h. The mixture was filtered through a pad of silica gel and concentrated.

As an additional benefit, the 5-iodo-1,2,3-triazole adducts are versatile synthetic intermediates, which are amenable to further functionalization. Later, GarcíaÁlvarez [202], Rowan [203], Zhu [204], and Díez-González [205] independently reported the cycloaddition of azides with haloalkynes under copper catalysis. 5 mL) at room temperature for 20 min, after which time a homogeneous solution was obtained. 5 mL) and added in a single portion to the catalyst solution. The reaction mixture was stirred for 45 min, and then quenched by adding 10% NH4OH solution (1 mL).

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