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. 2012 Jan 1;45(1):3-16.

"Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature

Bruce H Lipshutz  1 , Subir Ghorai
Affiliations

"Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature

Bruce H Lipshutz et al. Aldrichimica Acta. .

Abstract

New methodologies are discussed that allow for several commonly used transition-metal-catalyzed coupling reactions to be conducted within aqueous micellar nanoparticles at ambient temperatures.

Keywords: PTS; TPGS-750-M; cross-couplings; designer surfactants; green chemistry; micellar catalysis.

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Figures

Figure 1
Figure 1
Ingredients of COREXIT® EC9500 (a Mixture of 1–5) and COREXIT® EC9527 (Includes 1–6). (Ref. 2b)
Figure 2
Figure 2
Polyoxyethanyl-α-tocopheryl Sebacate (PTS, 7) and TPGS-1000. (Ref. 8,13)
Figure 3
Figure 3
Cryo-TEM Data Comparing Nanoparticles of PTS (A) and TPGS-1000 (B). (Ref. 8,14)
Figure 4
Figure 4
PTS-Enabled Reactions in Water at Room Temperature.
Figure 5
Figure 5
Ligands and/or Catalysts Used in Coupling Reactions. (Ref. 25)
Figure 6
Figure 6
Pictorial Account of Couplings of RZnX in Water: Timing Is Key.
Figure 7
Figure 7
Cryo-TEM Image of (A) Aqueous PTS (50-nm Scale), (B) Aqueous PTS in the Presence of 3 M NaCl (100-nm Scale), and (C) TPGS-750-M. (Ref. 54)
Figure 8
Figure 8
Structures of TPGS, PTS, and the Newly Engineered TPGS-750-M. (Ref. 63)
Figure 9
Figure 9
Nonracemic Ligands Used in CuH-Catalyzed Asymmetric Hydrosilylation.
Figure 10
Figure 10
Structure of “Nok” (SPGS-550-M) Currently under Study.
Scheme 1
Scheme 1
Recent Examples of the Heck Coupling in Water. (Ref. 60–62)
Scheme 2
Scheme 2
Two Examples of the Influence of Added Salt on the Outcome of the Heck Coupling in PTS–H2O. (Ref. 54)
Scheme 3
Scheme 3
Straightforward, High-Yield Synthesis of TPGS-750-M. (Ref. 63)
Scheme 4
Scheme 4
Cross-Couplings in PTS–H2O and in TPGS-750-M–H2O. (Ref. 63)
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