Ag2CO3 is the key: The transition‐metal‐catalyzed cycloaddition of isocyanides and unactivated terminal alkynes has been realized with Ag2CO3 as a unique and robust catalyst (see scheme). The protocol is highly efficient, allowing a broad range of terminal and internal alkynes to react under base‐ and ligand‐free conditions, generating synthetically useful oligosubstituted pyrroles in high yields.
A copper(I)-catalyzed, regioselective C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds using Togni's reagent was developed. Diverse substrates, including enones as well as α,β-unsaturated esters, thioesters, and amides, stereospecifically afforded the corresponding (E)-α-trifluoromethylated products in moderate to high yields. Further, this method was applied to the C-H trifluoromethylation of drugs.
The acidic hierarchical zeolite ZSM-5 (HZSM-5-H) was synthesized for the preparation of a supported Ru catalyst (Ru/HZSM-5-H). The obtained Ru/HZSM-5-H catalyst shows high activity and product selectivity in the seleno-functionalization of alkenes compared to g-Al 2 O 3 , basic ETS-10 and acidic microporous zeolite ZSM-5 supported Ru catalysts (Ru/g-Al 2 O 3 , Ru/ETS-10 and Ru/HZSM-5, respectively), as well as a homogeneous RuCl 3 catalyst. The relatively strong acidic sites in Ru/HZSM-5-H could benefit the adsorption of styrenes and the activation of the C]C bond. Meanwhile, Ru 4+ in Ru/HZSM-5-H could facilitate the formation of electrophilic selenium species as compared to Ru 0 species. In addition, the Ru/ HZSM-5-M catalyst exhibits broad substrate compatibility in the difunctionalization of alkenes.
Cyclopentadienes are valuable intermediates in organic synthesis and also ubiquitous as the Cp ligands in organometallic chemistry. As part of ongoing efforts to develop novel organic reactions that employ functionalized alkynes, a [3+2] cycloaddition of propargylic alcohols and ketene dithioacetals has been developed, which leads to fully substituted 2,5-dialkylthio cyclopentadienes in good to excellent yields. In an unusual dethiolating Diels-Alder reaction, the cyclopentadienes were further reacted with maleimides to afford a family of novel fluorescent polycyclic compounds.
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