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Sugar-Incorporated N-Heterocyclic Carbene Complexes

Sugar-Incorporated N-Heterocyclic Carbene Complexes Takanori Nishioka,* Teppei Shibata, and Isamu Kinoshita* Organometallics 2007, 26, 1126-1128. Chem. Commun. 2006 ,4392-4393. Hydrophilic part. cat. 3. Sodium dodecyl sulfate ( SDS ). C 12 H 25 NaO 4 S.

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Sugar-Incorporated N-Heterocyclic Carbene Complexes

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  1. Sugar-Incorporated N-Heterocyclic Carbene Complexes Takanori Nishioka,* Teppei Shibata, and Isamu Kinoshita* Organometallics 2007, 26, 1126-1128

  2. Chem. Commun. 2006,4392-4393.

  3. Hydrophilic part cat. 3 Sodium dodecyl sulfate (SDS) C12H25NaO4S J. Org.Chem. 1999, 64, 5593.

  4. Bioorg. Med. Chem. Lett. 2004, 14, 2533.

  5. OlefinMetathesis Grubbs’ catalyst Acc. Chem. Res. 2001, 34, 18-29

  6. Hydrogenation Chem. Commun. 2002, 2518.

  7. Hydrogen Transfer Organometallics2004, 23, 629.

  8. Hydroformylation

  9. Hydrosilylation Science 2002, 298, 204.

  10. H/D exchange reaction J. Am. Chem. Soc. 2006, 128, 3974.

  11. 1-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl) imidazolium bromide CH3CN 31% 4.5 h DMSO acetone [Ag(magi)2](AgBr2) 2

  12. Transmetalation J. Organomet. Chem. 2005, 690, 5451. J. Organomet. Chem. 2000, 600,12.

  13. AgCl Organometallics 2005, 24, 6301.

  14. [Ir-BM] [Ir-Me4]

  15. 95 %

  16. 100 %

  17. Conclusion 1. Synthesis of the first examples of saccharide-incorporated NHC ligand precursor and saccharide-incorporated NHC transition-metal complexes. 2. The X-ray structure of the Ir complex had almost the same coordination geometry as other Ir NHC complexes 3. Saccharide-incorporated NHC ligands should make it possible to develop new drugs and novel catalysts for syntheses in water Goal • Many kinds of bromosaccharides are available, our method can be used to • synthesize other metal complexes having NHC ligands with a variety of • saccharides. • 2. Syntheses of other transition-metal complexes using the Ag complexes as a • carbene transfer agentare.

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