10.1021/ja206339s.s001 Rebecca L. Simmons Rebecca L. Simmons Robert T. Yu Robert T. Yu Andrew G. Myers Andrew G. Myers Storable Arylpalladium(II) Reagents for Alkene Labeling in Aqueous Media American Chemical Society 2011 Aqueous MediaWe show Arylpalladium acid Alkene indocyanine dye residues organometallic intermediates decarboxylative palladation Reagent arylpalladium dimethyl sulfoxide reagent biotin derivative Storable benzoic solution olefinic substrates 2011-10-12 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Storable_Arylpalladium_II_Reagents_for_Alkene_Labeling_in_Aqueous_Media/2603233 We show that arylpalladium(II) reagents linked to biotin and indocyanine dye residues can be prepared by decarboxylative palladation of appropriately substituted electron-rich benzoic acid derivatives. When prepared under the conditions described, these organometallic intermediates are tolerant of air and water, can be stored for several months in solution in dimethyl sulfoxide, and permit biotin- and indocyanine dye-labeling of functionally complex olefinic substrates in water by Heck-type coupling reactions.