Phenolic compounds trifluoromethanesulfonate

In addition to halides, some pseudohalides undergo facile oxidative addition to Pd and Ni complexes. Trifluoromethanesulfonates (triflates), namely aiyl triflates 3 derived from phenols and enol triflates of carbonyl compounds, are most useful. 

A,iV-DIMETHYLMETHANIDE (68-12-2) Forms explosive mixture with air (flash point 136°F/58 C). Violent reaction with nitrates, carbon tetrachloride, hexachlorocyclohexane, and other halogenated compounds, particularly in contact with iron or strong oxidizers, may cause fire and explosions. Vigorous reaction with alkylaluminums. Incompatible strong acids, allyl trifluoromethanesulfonates, ammonia, chlorinated hydrocarbons, cresols, chromic anhydride, isocyanates, nitrates, phenols, magnesium nitrate, methylene diisocyante, phosphorous trioxide, triethyl aluminum. Attacks some plastics and coatings. 

Kita and coworkers reported a novel method to prepare 2,2 -substituted biphenyl compounds using phenyliodine(III) bis(trifluoroacetate) (FIFA), a hypervalent iodine reagent. The substrate for the coupling was first prepared by reacting 1 equiv of di-f-butylsilyl bis(trifluoromethanesulfonate) with 2 equiv of the phenol 46. Di-f-butylsilylene 47 then underwent an intramolecular cyclization in the presence of BF3 -OEt2 to provide the desired tricyclic compound 48. Removal of silylene ether was accomplished by TBAF in excellent yields. This sequence worked well for both 2,2 -disubstituted symmetrical and unsymmetrical biphenyls (eq 17). ... 

---