Table 2.
Activation of Glycosyl Fluoride Donors
| promoter | additive | |
|---|---|---|
| tin- and silicon-based reagents | ||
| SnCl28,420 | AgClO4,8,451 TrClO4,420 AgOTf,451,452 AgB(C6F5)4451,453,454 | |
| SnCl4455 | AgB(C6F5)4453 | |
| SnF4456 | ||
| R3SnCl or R2SnCl2457 | AgClO4457 | |
| Sn(OTf)2458 | BF3-Et2O, TiCl4, La(OTf)3, Yb(OTf)3 or La(ClO4)3-nH2O459 | |
| SiF4404 | ||
| CF3SO3SiMe3404,456,460 | ||
| SiCl4 or Ph3SiCl453 | AgB(C6F5)4453 | |
| boron-, aluminum-, and gallium-based reagents | ||
| BF3-Et2O423,455,461 | ||
| TrB (C6F5)4462,463 | ||
| HB(C6F5)4464,465 | ||
| B(C6F5)3466 | ||
| AlMe3455 | ||
| Me2GaCl, Me2GaOTf or MeGa(OTf)2467 | ||
| main group metal salts | ||
| MgBr2-Et2O455 | ||
| LiClO4468,469 | CsF468,469 | |
| CaBr2 or Ca(NO3)2470 | NMe3470 | |
| Ca(OTf)2470 | NMe3470,471 | |
| Ca(OH)2471 | ||
| transition metal salts | ||
| TiF4456,460 | AgClO4,472 AgBF4473 | |
| Cp2TiCl2474 | AgClO4474 AgB(C6F5)4453 | |
| TiCl2453 | AgB(C6F5)4453 | |
| Cp2ZrCl2474 | AgClO4474,475 AgOTf, AgBF4, AgPF6 or AgSbF6,475 AgB(C6F5)4453 | |
| SO4/ZrO2476 | ||
| Cp2HfCl2474 | AgClO4,474,477,478 AgB(C6F5)4453 | |
| Hf(OTf)4479 | ||
| Cu(OTf)2480 | ||
| lanthanide metal salts | ||
| Yb(OTf)3481 | K2CO3,481,482 CaCO3, K2CO3/ ZnCl2 or K2CO3/Ba(ClO4)2481 | |
| YbCl3481 | CaCO3481 | |
| Yb-Amberlyst-15483 | ||
| Yb[N(O2SC4F9)2]3484 | ||
| La(ClO4)3-7H2O481,482 | K2CO3481,482 | |
| La(ClO4)3-nH2O, Pr(ClO4)3-nH2O, or Eu(ClO4)3-nH2O482 | K2CO3482 | |
| Ce(ClO4)3-nH2O482,485 | K2CO3482,485 | |
| anhydrides, protic acids, and other reagents | ||
| Tf2O460 | ||
| TfOH465,486–488 | ||
| HClO4, HOSO2C4F9, HNTf2 or HSbF6464–465 | ||
| RN+B(C6F5)4, RN+OTf, RN+SbF6, RN+BF4 or RN+ClO4489 | ||
| solvolysis490 | ||