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Lipshutz Group – Professor Product Portal

Professor Product Portal Index

Professor Bruce Lipshutz Professor Bruce Lipshutz

Congratulations to Prof. Lipshutz on his recent accomplishments!

*2016 Organic Letters Outstanding Publication of the Year Lectureship Award.
Read about the award and paper, and then check out TPGS-750-M below.

*2011 Presidential Green Chemistry Challenge Award. Learn more.

Prof. Bruce Lipshutz and co-workers have developed designer surfactants to allow several classes of transformations (e.g. Suzuki-Miyaura, Olefin Metathesis, 1,4-Addition to Enones, etc.) to be performed in water. Three generations –  PTS, TPGS-750-M (neat and aqueous solution), and Nok – are available through Aldrich and encapsulate the reactive species within a micelle, allowing for efficient reactivity at room temperature.

Prof. Lipshutz is also known for work with organocopper reagents. Some have been commercialized, including the "cuprate in a bottle" (324175) and "CuH in a bottle" (762458).  His group has contributed several reagents that are used routinely in the community, such as the SEM protecting group precursor SEM-Cl (238902) and Mitsunobu coupling reagent DCAD (680850) as a recoverable alternative to DEAD.

Lipshutz Group website
Link to Aldrichimica Acta review (2015)

Products available at Aldrich from the Lipshutz Laboratory

     
Bruce H. Lipshutz, Fabrice Gallou, Sachin Handa
ACS Sustainable Chem. Eng.
An overview is presented on the unfortunate use of organic solvents as the traditional medium in which organic synthesis has been, and continues to be, practiced. An argument is made, from the environmental perspective, for a long overdue switch to alternative reaction media, and water in particular, following Nature's lead...Read More

Piyatida Klumphu, Bruce H Lipshutz
Journal of Organic Chemistry 2014-02-07
The third-generation designer amphiphile/surfactant, "Nok" (i.e., SPGS-550-M; β-sitosterol methoxypolyethyleneglycol succinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock and β-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in wate...Read More
Ralph Moser, Subir Ghorai, Bruce H Lipshutz
Journal of Organic Chemistry 2012-04-06
Described herein are newly developed, straightforward entries to polyethyleneglycol ubiquinol succinate (PQS, n = 2), a designer surfactant that serves as precursor to micelle-forming, covalently bound catalysts for a variety of transformations in water with in-flask catalyst recycling.Read More
Guo-ping Lu, Karl R Voigtritter, Chun Cai, Bruce H Lipshutz
Chemical Communications 2012-09-07
Unexpected losses in stereochemistry from Stille reactions involving Z-alkenyl halides have been shown to be ligand dependent. A new set of reaction conditions has been developed that, in most cases, leads to highly stereoselective cross-couplings under mild conditions, along with improved yields.Read More
Guo-Ping Lu, Karl R Voigtritter, Chun Cai, Bruce H Lipshutz
Journal of Organic Chemistry 2012-04-20
The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geomet...Read More
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