Trifluoromethoxylation/trifluoromethylthiolation/trifluoro- methylselenolation strategy for the construction of heterocycles

Tf2O‐Catalyzed Tandem Cyclization/Trifluoromethylselenolation of Alkynes for Synthesis of CF3Se‐Containing Heterocycles

“…( 4)). Besides, TfOH generated from the reaction between Tf 2 O and EtOH is probably the real catalytic species (Table 1, entries [14][15][16]. Based on the above experiments and previous reports, [22,23a,b]…”

“…Hence, synthetic methodologies for accessing CF 3 Se-containing heterocycles are in great demand. [16] Electrophilic cyclization of alkynes with trifluoromethylselenolation reagents has been an ingenious strategy for preparation of CF 3 Se-containing heterocycles. Billard and coworkers developed the metal-free approach to CF 3 Se-containing benzofurans/benzothiophenes and isoquinoline by using the in-situ formed CF 3 SeCl (Scheme 1b, Equation (1)).…”

Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

“…Due to the unique properties of the CF 3 Se group, namely its high lipophilicity and strong electron-withdrawing effect, 9 considerable efforts have been devoted to its direct incorporation into alkynes. 10,11 However, only a few methods are available for synthesizing trifluoromethylselenolated alkynes. For example, Billard 9 a and Tlili 12 reported electrophilic trifluoromethylselenolations of an alkynyl lithium and alkynyl copper (Scheme 1-1a).…”

Lewis Acid Promoted Vicinal Oxytrifluoromethylselenolation of Alkenes

“…In addition, the CF 3 Se group, exhibiting enhanced lipophilicity and bioactivity by incorporating into organic molecules, has been emerging as an elegant motif in the design of drug candidates . Therefore, the efficient approaches to CF 3 Se-containing compounds have gained extensive interest …”