Potassium (1‐Organo‐1H‐1,2,3‐triazol‐4‐yl)trifluoroborates from Ethynyltrifluoro­borate through a Regioselective One‐Pot Cu‐Catalyzed Azide–Alkyne Cycloaddition Reaction

Decade Advances of NaN3 in Three‐component Reactions

“…Commonly, the thermal [3+2] cycloaddition could not perfectly control the regioselectivity for 1,4‐ and 1,5‐disubstituted 1,2,3‐triazoles. The Ham group [20b] depicted the application of potassium ethynyltrifluoroborate in CuAAC. Organotrifluoroborate products were recommended for further cross‐coupling reaction.…”

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

“…The inertness of the trifluoroborate (-BF 3 ) group under common reaction conditions for direct transformation, using Pd or copper catalysts, enables the preparation of highly functionalized organotrifluoroborates to be performed [53,54]. In this context, Kim et al [55] have recently described a sustainable MW assisted SMC process which starts from various triazole-containing trifluoroborates and which was successfully prepared via a regioselective, one-pot Cu-catalyzed azide/alkyne cycloaddition (CuAAC) reaction from ethynyltrifluoroborate. Potassium (1-organo-1H-1,2,3-triazol-4-yl)trifluoroborates were successfully cross-coupled with various functionalized aryl and alkenyl bromides under MW conditions.…”

Recent Applications of Phosphane-based Palladium Catalysts in Suzuki-Miyaura Reactions Involved in Total Syntheses of Natural Products

“…[200] Phase-transfer glycosylation of the resulting alternariol 9-methyl ether (C43) with commercially available acetobromoglucose produced glycoside 295 (Figure 13), which was converted to lysilactone A (247) ( Figure 13) by treatment with sodium methoxide in MeOH. [200] In 2013, compound C45, which was prepared in 70% yield by Pd(OAc)2/SPhos-catalyzed reaction of A47 with aryl bromide B53 (entry 11, Table 7), was used as a key intermediate in a concise synthesis of the hasubanan alkaloid cepharatine A (250). [226] In particular, compound C45 was converted to O-alkylated biaryl 296 by treatment with the dibromide in situ generated by addition of bromine to ethyl vinyl ether.…”

“…pyran-6-one glycoside recently isolated from endophytic Aspergillus sp. Yxf3;[201] phenaglydon(249), an alkaloid isolated from Glycosmis cyanocarpa (Rutaceae);[202] racemic cepharatine A(250), an alkaloid which in levorotatory form was isolated from Stephania cepharantha (Menispermaceae);[203] and arylomycin A2 (251), a biaryl-bridged lipopeptide antibiotic produced by Streptomyces sp. Tu 6075 [204].…”