Table 1.
Activation of Glycosyl Bromide Donors
| promoter | additive |
|---|---|
| silver and copper salts | |
| Ag2CO36,7 | I2,153,220 Lewis acid221 |
| AgNO37,151 | crown ether222,223 |
| AgOAc6,7 | |
| Ag2O151 | I2,154 borinic acid,224 HOFox/Lewis acid,217,225 TMSOTf,146,221,226 TfOH221 |
| AgClO4227–229 | |
| AgBF4227,230 | |
| AgPF6230 | |
| AgOTf230 | TMU231 |
| other organic Ag salts221,232–234 | TfOH221 |
| Ag silicate-alumina235 | |
| Ag zeolite236 | |
| Ag silica-alumina237 | |
| silver imidazole | ZnCl2238 |
| Ag2SO4 | TfOH,221,226 |
| CuI + BPhen + Xantphos147 |
DTBMP147 |
| mercury, zinc, and cadmium salts | |
| Hg(OCOCH3)2160,161 | |
| Hg(CN)2239 | HgBr2239 |
| HgO239 | HgBr2240 |
| HgBr2241,242 | |
| Hg(PhCOO)2243 | |
| Hg(NpCOO)2243 | |
| HgI2244 | |
| ZnO239 | |
| ZnCl2245,246 | TrCl;245 TMSCl247 |
| ZnBr2245,246 | TrBr;245 TMSBr246,247 |
| Zn(OTf)2 | TMSBr248 |
| CdO239 | |
| CdCO3249–251 | |
| CdS249 | |
| indium, tin, and bismuth salts | |
| InCl3252,253 | |
| InBr3253 | |
| InI3254 | |
| In(OTf)3254 | |
| In(NTf2)3254 | |
| SnCl4255 | |
| Sn(OTf)2 | base256 |
| PbCO3251 | |
| non-nucleophilic bases | |
| pyridine7,148,182,257 | |
| quinoline150,156 | |
| collidine180 | |
| phenanthroline derivatives257 | |
| 2,2′-bipyridine257 | |
| halogens or halide ions | |
| NR4Br258,259 | |
| I2260,261 | DDQ260 |
| IBr262,263 | DABCO262 |
| ICl263 | |
| NIS261,263 | I2;263 protic acids261 |
| other methods | |
| NR3264–266 | |
| PR3265,266 | |
| SR2265,266 | |
| solvolysis7,230,267,268 | NR4Br;267,268 silver salts230 |