A nanomicelle-forming amphiphile """"""""PTS"""""""" has been identified that allows for several Pd- and Ru-catalyzed cross-couplings to take place in water as the only solvent, and at room temperature, in high isolated yields. The new processes include Heck, Suzuki, Sonogashira, and olefin cross-metathesis reactions, where product isolation is especially facile. Several additional studies are planned based on the """"""""micellar effect."""""""" The notion of """"""""designer"""""""" surfactants applied to organometallic catalysis is advanced in this proposal, and represents a variable essentially overlooked by the synthetic community. This technology also is to be applied to other important cross-couplings, such as aminations and asymmetric additions of hydride to Michael acceptors, all in water at room temperature.

Public Health Relevance

Selected common transition metal-catalyzed reactions normally run in organic solvents can be done in pure water using an inexpensive and readily available, nanoparticle- forming, additive. These reactions also benefit in that they can be conducted at room temperature, thus requiring no external input of energy. In a broader sense, the technology is potentially valuable as a contribution to green chemistry

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
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Synthetic and Biological Chemistry B Study Section (SBCB)
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Schwab, John M
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University of California Santa Barbara
Schools of Arts and Sciences
Santa Barbara
United States
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Nishikata, Takashi; Abela, Alexander R; Huang, Shenlin et al. (2016) Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies. Beilstein J Org Chem 12:1040-64
Bhattacharjya, Anish; Klumphu, Piyatida; Lipshutz, Bruce H (2015) Ligand-free, palladium-catalyzed dihydrogen generation from TMDS: dehalogenation of aryl halides on water. Org Lett 17:1122-5
Handa, Sachin; Slack, Eric D; Lipshutz, Bruce H (2015) Nanonickel-catalyzed Suzuki-Miyaura cross-couplings in water. Angew Chem Int Ed Engl 54:11994-8
Bhattacharjya, Anish; Klumphu, Piyatida; Lipshutz, Bruce H (2015) Kumada-Grignard-type biaryl couplings on water. Nat Commun 6:7401
Isley, Nicholas A; Hageman, Matt S; Lipshutz, Bruce H (2015) Dehalogenation of Functionalized Alkyl Halides in Water at Room Temperature. Green Chem 2015:307
Fennewald, James C; Landstrom, Evan B; Lipshutz, Bruce H (2015) Reductions of aryl bromides in water at room temperature. Tetrahedron Lett 56:3608-3611
Krasovskiy, Arkady L; Haley, Stephen; Voigtritter, Karl et al. (2014) Stereoretentive Pd-catalyzed Kumada-Corriu couplings of alkenyl halides at room temperature. Org Lett 16:4066-9
Handa, Sachin; Fennewald, James C; Lipshutz, Bruce H (2014) Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature. Angew Chem Int Ed Engl 53:3432-5
Lipshutz, Bruce H; Ghorai, Subir (2014) Transitioning organic synthesis from organic solvents to water. What's your E Factor? Green Chem 16:3660-3679
Slack, Eric D; Gabriel, Christopher M; Lipshutz, Bruce H (2014) A palladium nanoparticle-nanomicelle combination for the stereoselective semihydrogenation of alkynes in water at room temperature. Angew Chem Int Ed Engl 53:14051-4

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