Intramolecular Heck-type reactions in aqueous medium. Dramatic change in regioselectivity

Lemaire‐Audoire, Sandrine; Savignac, Monique; Dupuis, Christophe; Genêt, Jean‐Pierre

doi:10.1016/0040-4039(96)00253-5

Cited by 66 publications

(13 citation statements)

References 21 publications

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“…Mizoroki–Heck and Sonogashira reaction conditions were screened by using the iF peptide (Tables 1 and 2, and http://www.wiley-vch.de/contents/jc_2268/2007/f600432_s.pdf in the Supporting Information) 2. The optimal combination of catalyst and ligand was Pd(OAc) 2 and triphenylphosphine‐3,3′,3′′‐trisulfonate (TPPTS) 13. 14 We confirmed that both of the reactions proceeded at low temperature (<5 °C) in the presence of a protein (BSA); this suggests that a protein substrate can be subjected to organopalladium reactions.…”

Section: Resultsmentioning

confidence: 62%

Site‐Specific Functionalization of Proteins by Organopalladium Reactions

et al. 2007

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A new carbon-carbon bond has been regioselectively introduced into a target position (position 32 or 174) of the Ras protein by two types of organopalladium reactions (Mizoroki-Heck and Sonogashira reactions). Reaction conditions were screened by using a model peptide, and the stability of the Ras protein under the reaction conditions was examined by using the wild-type Ras protein. Finally, the iF-Ras proteins containing a 4-iodo-L-phenylalanine residue were subjected to organopalladium reactions with vinylated or propargylated biotin. Site-specific biotinylations of the Ras protein were confirmed by Western blot and LC-MS/MS.

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Section: Resultsmentioning

confidence: 62%

Site‐Specific Functionalization of Proteins by Organopalladium Reactions

et al. 2007

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“…Previously, the same observations with increase of 1,2 product going from organic to water media were observed in intramolecular Mizoroki-Heck reaction. 32 (Sigma-Aldrich, USA) at 298 K with at least three experiments for each system. Statistical data treatment was done using t-Student coefficient and the particle size determination error was <2%.…”

Section: Catalytic Activities Of Cross-linked Polymer In Mizoroki-heck Reactionmentioning

confidence: 99%

New poly-imidazolium–triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles – a prospective support for Pd in the Mizoroki–Heck reaction

et al. 2021

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“…The simple catalyst separation is an important step towards the development of environmentally friendly industrial processes. There is a wide variety of literature on Mizoroki-Heck reactions with TPPTS or related water-soluble phosphine salts 55-63 ( Figure 15.5) in aqueous organic solvents [156][157][158][159][160][161][162][163][164][165][166][167][168][169][170][171][172]. Ligand 56 was tested in various Mizoroki-Heck couplings and compared with a few other water-soluble ligands.…”

Section: Aqueous Systems With Additional Organic Solventmentioning

confidence: 99%