CsOH×H₂O in Organic Synthesis

Introduction

Cesium hydroxide monohydrate (CsOH˙H₂O) is an important reagent in organic synthesis being applied in a diversity of reactions. It is a solid strong base, commercially available, and it can be used in an assortment of solvents and reaction conditions.

Cesium hydroxide monohydrate allows the catalytic generation of highly reactive anions, which are able to add to carbonyl groups or carbon-carbon multiple bonds. Its great versatility as a base can be seen in a range of reactions as those involving carbon-carbon and carbon-­heteroatom bond formation. The increasing interest on CsOH˙H₂O over the last few years, is patent on the diversity of applications, and the increased number of publications reporting its powerful basicity.

References

• 1 Tzalis D. Knochel P. Angew. Chem. Int. Ed.  1999,  38:  1463 
• 2 Tzalis D. Koradin C. Knochel P. Tetrahedron Lett.  1999,  40:  6193 
• 3 Koradin C. Rodriguez A. Knochel P. Synlett  2000,  1452 
• 4a Andrus MB. Hicken EJ. Stephens JC. Bedke DK. J. Org. Chem.  2005,  70:  9470 
• 4b Corey EJ. Bo Y. Busch-Petersen J. J. Am. Chem. Soc.  1998,  120:  13000 
• 4c Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc.  1997,  119:  12414 
• 5 Housseman C. Zhu J. Synlett  2006,  1777 
• 6a Salvatore RN. Nagle AS. Jung KW. J. Org. Chem.  2002,  67:  674 
• 6b Salvatore RN. Schmidt SE. Shin S. Nagle AS. Worrell JH. Jung KW. Tetrahedron Lett.  2000,  41:  9705 
• 6c Salvatore RN. Nagle AS. Schmidt SE. Jung KW. Org. Lett.  1999,  1:  1893 
• 7a Varala R. Ramu E. Alam MM. Adapa SR. Synlett  2004,  1747 
• 7b Varala R. Ramu E. Alam MM. Adapa SR. Chem. Lett.  2004,  33:  1614 
• 7c Varala R. Ramu E. Adapa SR. Bull. Chem. Soc. Jpn.  2006,  79:  140 
• 8 Honaker MT. Sanderfur BJ. Hargett JL. McDaniel AL. Salvatore RN. Tetrahedron Lett.  2003,  44:  8373 
• 9 Liu Y. Li J. Zheng H. Xu D. Xu Z. Zhang Y. Synlett  2005,  2999