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Storable arylpalladium(II) reagents for alkene labeling in aqueous media.

ABSTRACT: 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.

SUBMITTER: Simmons RL

PROVIDER: S-EPMC3188328 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Storable arylpalladium(II) reagents for alkene labeling in aqueous media.

Simmons Rebecca L RL Yu Robert T RT Myers Andrew G AG

Journal of the American Chemical Society 20110915 40

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 coup ...[more]

PMID: 21888420

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