Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

• Benedek Batizi,
• Patrik Pollák,
• András Dancsó,
• Péter Keglevich,
• Gyula Simig,
• Balázs Volk and
• Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

• reactions: reduction of ring A of the β-carboline skeleton or trifluoroethylation of the pyrrole moiety occurred, leading to interesting and potentially useful derivatives. Keywords: alkaloid; β-carboline; Carex brevicollis DC; cross-coupling reaction; trifluoroethylation; Introduction Carex brevicollis

• -carbolines. Some surprising reactions were also observed, such as the unexpected formation of racemic tetrahydrobrevicolline and the trifluoroethylation of the pyrrole moiety, which can also serve as favorable starting points for further research. The structure of brevicolline ((S)-1) and brevicarine (2). X

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• easily available 2,2,2-trifluoroethyl(mesityl)iodonium triflate reagent enabled the straightforward trifluoroethylation of diverse sulfoxonium ylides under mild conditions and short reaction times. Various computational strategies were also employed to differentiate between competing halogen bond

• ylides can be derivatized using hypervalent iodine reagents, and our continued efforts towards this will be reported in due course. Experimental Representative procedure for 2,2,2-trifluoroethylation of sulfoxonium ylides An oven dried 5 mL microwave flask containing a magnetic stirrer was charged with

Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF₃

• Xueliang Jiang and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2013, 9, 2862–2865, doi:10.3762/bjoc.9.322

• -mediated trifluoroethylation of arylboronic acids [13][14] (Scheme 1a) and trifluoromethylation of benzyl halides [15][16][17][18][19][20][21] (Scheme 1b) are more convenient. Especially trifluoromethylations of benzyl bromides with a [CuCF3] species, which are generated from different precursors, are

Oxidative 3,3,3-trifluoropropylation of arylaldehydes

• Akari Ikeda,
• Masaaki Omote,
• Shiho Nomura,
• Miyuu Tanaka,
• Atsushi Tarui,
• Kazuyuki Sato and
• Akira Ando

Beilstein J. Org. Chem. 2013, 9, 2417–2421, doi:10.3762/bjoc.9.279

• , the 2,2,2-trifluoroethylation and the 3,3,3-trifluoropropylation, which elongate the product by two and three carbon atoms, respectively, have not been explored yet. 2-Bromo-3,3,3-trifluoropropene [14][15][16][17][18][19][20][21][22][23][24][25][26] and 1,1,1,3,3-pentafluoropropane [27][28] have been