Friedel–Crafts Benzylation and Phenethylation Reactions Using Benzyl and Phenethyl Benzothiazol-2-yl Carbonate Derivatives

Abstract

Friedel–Crafts benzylation and phenethylation reactions of several aromatic compounds with benzyl and phenethyl benzothiazol-2-yl carbonate derivatives were carried out in the presence of scandium triflate (Sc(OTf)3) as a catalyst. Suitable combinations of the leaving group of carbonates and acid promoters that generate cationic alkyl species were examined.

Synthesis and Structure of a New Tetrakis(pentafluorophenyl)borate Salt of the Silver(I) Cation with Novel Trigonal Planar Tris(benzene) Coordination

“…Thus, except for patents, 5 reports of Ag + TPFPBare quite limited. To the best of our knowledge, this Ag + salt has been reported as a catalyst only in glycosylation 6 or Friedel-Crafts reactions, 7 and no X-ray structures of Ag + TPFPBwith aromatic ligands have been reported. 8 Here we report on the preparation of the TPFPBsalt of a new silver(I) complex, Ag(C 6 H 6 ) 3 + -TPFPB -(1), and its X-ray structure, clearly demonstrating the presence of a silver ion coordinated with three benzene molecules in a trigonal planar fashion.…”

“…(b) Two additional views of the cation moiety. Selected bond lengths (Å): Ag-C1 ) 2.391(6), Ag-C2 ) 2.660(6), Ag-C7 ) 2.398(7), Ag-C8 ) 2.737(8), Ag-C13 ) 2.400(6), Ag-C14 ) 2.646(6). Selected angles (deg): C1-Ag-C7 ) 119.7(2), C1-Ag-C13 ) 122.4(2), C7-Ag-C13 ) 117.9(2), C2-C1-Ag ) 84.8(4), C6-C1-Ag ) 93.1(4), C12-C7-Ag ) 91.7(4), C8-C7-Ag ) 88.2(4), C14-C13-Ag ) 83.9(4), C18-C13-Ag ) 92.2(4).…”

Fe/CuBr2-Catalyzed Benzylation of Arenes and Thiophenes with Benzyl Alcohols

“…For examples, lanthanide and actinide triflates have been used as catalysts. [13][14][15][16][17][18][19] Beller and co-workers demonstrated the use of RhCl 3 , IrCl 3 , H 2 PdCl 4 , H 2 PtCl 6 , FeCl 3 , HAuCl 4 , and AuCl 3 to promote catalytic benzylation. [20][21][22] Rueping also reported another catalytic system with Bi(OTf) 3 .…”