Silver Carbonate

Introduction

Silver carbonate, Ag₂CO₃, is a odorless, yellow to yellow-grey powder poorly soluble in water. Upon heating, it gradually decomposes to silver oxide, Ag₂O, and CO₂ close to its melting point of 210 ˚C. Silver carbonate is commercially available, but can also be readily accessed through the reaction of cheaper silver nitrate with sodium carbonate in water (Scheme  [¹] ). [¹]

Scheme 1 Silver carbonate is easily obtained from silver nitrate and sodium carbonate

Silver carbonate can also be used to prepare other silver salts. One such salt, particularly useful in catalysis is silver bis(trifluoromethanesulfonyl)imide, derived from the reaction of silver carbonate and triflimide (Scheme  [²] ). [²]

Scheme 2 Silver carbonate can also be used for the preparation of other useful silver salts

Silver carbonate has found a myriad of different uses in organic chemistry, notably as oxidizing agent (Fetizon’s reagent), as catalyst for alkyne activation, as halogen scavenger and as base and/or oxidant of choice for various transition-metal-catalyzed reactions. Selected applications of silver carbonate in these diverse contexts will be presented here.

References

• 1For a detailed protocol see:
• 1 Xu C. Liu Y. Huang B. Li H. Qin X. Zhang X. Dai Y. Appl. Surf. Sci.   2011,  257:  8732 
• 2For a detailed protocol see:
• 2 Vij A. Zheng Y. Kirchmeier RL. Shreeve JM. Inorg. Chem.  1994,  33:  3281 
• 3 Tojo G. Fernández M. Oxidation of Alcohols to Aldehydes and Ketones   Springer Science; Business Media; New York: 2006. 
• 4 Takahashi K. Watanabe M. Honda T. Angew. Chem. Int. Ed.  2008,  131 
• 5 Other examples using stoichiometric amounts of Ag₂CO₃ have also been reported: Pale P. Chuche J. Eur. J. Org. Chem.  2000,  1019 
• 6 Rammah MM. Othman M. Ciamala K. Strohmann C. Rammah MB. Tetrahedron  2008,  64:  3505 
• 7a Del Buttero P. Molteni G. Pilati T. Tetrahedron: Asymmetry  2010,  21:  2607 
• In this same context, see also:
• 7b Lee KJ. Choi J.-K. Yum EK. Cho SY. Tetrahedron Lett.  2009,  50:  6698 
• 8 Chen K. Baran P. Nature  2009,  459:  824 
• 9This can be seen as a particular case of a more general concept coined as asymmetric counteranion-directed catalysis. For a leading reference, see:
• 9 Mayer S. List B. Angew. Chem. Int. Ed.  2006,  45:  4193 
• 10 Hamilton G. Kanai T. Toste FD. J. Am. Chem. Soc.  2008,  130:  14984 
• 11a Wang C. Piel I. Glorius F. J. Am. Chem. Soc.  2009,  131:  4194 
• For an intermolecular version, see:
• 11b Zhang F. Greaney MF. Org. Lett.  2010,  12:  4745 
• 12For a leading reference in this area see:
• 12 Murai S. Kakiuchi S. Sekine S. Tanaka Y. Kamatani A. Sonoda M. Chatani N. Nature  1993,  366:  529 
• 13 Wang F. Song G. Li X. Org. Lett.  2010,  12:  5430