A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.
A new and efficient strategy for the synthesis of tetraaryl-substituted olefins has been developed. With a Cu/Pd-catalyzed isomerization/insertion/oxidative coupling cascade reaction of cyclopropene with internal alkynes, a wide variety of cis-tetrasubstituted olefins were synthesized in good yields as single stereoisomers. The photophysical properties of these novel tetraarylethenes were fully characterized and proved to be good AIE (aggregation-induced emission) luminogens. Experimental studies and theoretical calculation indicated that Cu(I) and Pd(II) were the actual catalysts. A novel deprotonative Cu-catalyzed cyclopropene cycloisomerization and subsequent successive Cu/Pd transmetalation relay mechanism was proposed for the discovered reaction. † Electronic supplementary information (ESI) available: Detailed experimental procedures and analytical data. CCDC 1021785-1021787. For ESI and crystallographic data in CIF or other electronic format see
Transmetalation is a key step in traditional coupling reactions. Herein we discuss the most recent progress in the metal-metal relay catalysis based on a transmetalation strategy. An efficient synthetic strategy for the formation of polysubstituted furan derivatives from cyclopropenes based on the tandem metal relay catalysis (TMRC reaction) is summarized.
An efficient synthesis of bifurans via dimerization of cyclopropenes has been successfully developed using a copper-promoted cycloisomerization and palladium-catalyzed dimerization cascade. These novel bifuran structures possess interesting optoelectronic properties.
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