Bruce H. Lipshutz Explained

Bruce H. Lipshutz (born 1951) is an American chemist. He is a professor at the University of California, Santa Barbara.^[1]

Biography

Lipshutz received his undergraduate degree in chemistry from Binghamton University in 1973. His graduate work was supervised by Harry H. Wasserman at Yale. After a PhD degree in 1977, he spent two years at Harvard as a post-doctoral researcher in the group of Nobel Laureate E. J. Corey. Soon after, he accepted a position of Assistant Professor at UCSB rising to the ranks of Professor in 1987. He has received the Alfred P. Sloan Foundation Fellowship and the Camille & Henry Dreyfus Teacher-Scholar Award. In 2011 he was awarded Presidential Green Chemistry Award.^[2] He is Co-founder of Zymes LLC.^[3]

Contributions

Reagents

• Aqueous Micellar Catalysis using TPGS-750-M^[4] and Nok.^[5]
• Sustainable Palladium catalysis.^{[6] [7]}
• 2-(Trimethylsilyl)ethoxymethyl chloride

hydroxyl protecting group, selectively cleaved with fluoride ion under mild conditions.^[8]

• Di-(4-chlorobenzyl)azodicarboxylate (DCAD)

recyclable and convenient alternative to diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD) in Mitsunobu reaction.^[9]

• Ligated copper hydride.^{[10] [11]}
• Heterogeneous catalysts: nickel-on-charcoal, copper-on-charcoal, nickel-in-graphite, copper+nickel-on-charcoal.

Methodologies

• Higher-order organocuprates (Lipshutz cuprates).^[12]
• Chiral and achiral conjugate reductions.
• Catalyst development for ppm Pd-catalyzed C-C couplings in water at ambient^[13]
• Use of nonionic amphiphiles for transition metal-mediated cross coupling in organic synthesis.^[14]
• Low-cost synthesis of Coenzyme Q10.^{[15] [16]}

Notes and References

1. Web site: People | Department of Chemistry - UC Santa Barbara. www.chem.ucsb.edu.
2. Web site: Past Award Entries and Recipients | Green Chemistry | US EPA. 12 August 2023.
3. Web site: Zymes llc. https://web.archive.org/web/20080717023707/http://www.zymesllc.com/about/management-team/. dead. July 17, 2008.
4. 10.1021/jo101974u . TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature . 2011 . Lipshutz . Bruce H. . Ghorai . Subir . Abela . Alexander R. . Moser . Ralph . Nishikata . Takashi . Duplais . Christophe . Krasovskiy . Arkady . Gaston . Ricky D. . Gadwood . Robert C. . The Journal of Organic Chemistry . 76 . 11 . 4379–4391 . 21548658 . 3608414 .
5. 10.1021/jo401744b . "Nok": A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature . 2014 . Klumphu . Piyatida . Lipshutz . Bruce H. . The Journal of Organic Chemistry . 79 . 3 . 888–900 . 24447127 . 4013797 .
6. Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water . 10.1126/science.aac6936 . 2015 . Handa . Sachin . Wang . Ye . Gallou . Fabrice . Lipshutz . Bruce H. . Science . 349 . 6252 . 1087–1091 . 26339028 . 2015Sci...349.1087H .
7. 10.1002/anie.201510570 . HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature . 2016 . Handa . Sachin . Andersson . Martin P. . Gallou . Fabrice . Reilly . John . Lipshutz . Bruce H. . Angewandte Chemie International Edition . 55 . 16 . 4914–4918 . 26924396 . 4966530 .
8. β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group . 10.1016/S0040-4039(00)78684-9 . Tetrahedron Letters . January 1980 . 21 . 35 . 3343–3346 . Lipshutz . Bruce H. . Pegram . Joseph J. .
9. Simplification of the Mitsunobu Reaction. Di- p -chlorobenzyl Azodicarboxylate: A New Azodicarboxylate . 10.1021/ol0618757 . 2006 . Lipshutz . Bruce H. . Chung . David W. . Rich . Brian . Corral . Ricardo . Organic Letters . 8 . 22 . 5069–5072 . 17048845 .
10. (BDP)CuH: A "Hot" Stryker's Reagent for Use in Achiral Conjugate Reductions . 10.1021/ol702689v . 2008 . Baker . Benjamin A. . Bošković . Žarko V. . Lipshutz . Bruce H. . Organic Letters . 10 . 2 . 289–292 . 18092793 .
11. Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis - phosphine Ligands . 10.1021/ja021391f . 2003 . Lipshutz . Bruce H. . Noson . Kevin . Chrisman . Will . Lower . Asher . Journal of the American Chemical Society . 125 . 29 . 8779–8789 . 12862472 .
12. 10.15227/orgsyn.069.0080 . Mixed higher-order cyanocuprate-induced epoxide openings: 1-benzyloxy-4-penten-2-ol . Organic Syntheses . 1990 . 69 . 80 .
13. Evan Phos: A ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water. 10.1039/C8GC01356J. 2018. Landstrom. Evan B.. Handa. Sachin. Aue. Donald H.. Gallou. Fabrice. Lipshutz. Bruce H.. Green Chemistry. 20. 15. 3436–3443.
14. Web site: Merck KGaA . 2019-06-16 . 2016-11-12 . https://web.archive.org/web/20161112033834/http://www.sigmaaldrich.com/ifb/acta/v41/acta-vol41-2008.html#73/z . dead .
15. Web site: NSF - OLPA - News Tip: November 29, 2002. www.nsf.gov.
16. 10.1021/ol051329y. 16146360. An Improved Synthesis of the "Miracle Nutrient" Coenzyme Q10. Organic Letters. 7. 19. 4095–4097. 2005. Lipshutz. Bruce H.. Lower. Asher. Berl. Volker. Schein. Karin. Wetterich. Frank.