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] [14]}
• Use of nonionic amphiphiles for transition metal-mediated cross coupling in organic synthesis.^[15]
• Low-cost synthesis of Coenzyme Q10.^{[16] [17]}

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. TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature http://pubs.acs.org/doi/abs/10.1021/jo101974u
5. “Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature http://pubs.acs.org/doi/abs/10.1021/jo401744b
6. Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water https://www.science.org/doi/10.1126/science.aac6936
7. HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature http://onlinelibrary.wiley.com/doi/10.1002/anie.201510570/abstract
8. β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group https://archive.today/20120910143905/http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-42M7VH1-CX&_user=112642&_coverDate=12/31/1980&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000059608&_version=1&_urlVersion=0&_userid=112642&md5=281d979f2a9d8fc5ae34fd5005488c7d
9. Simplification of the Mitsunobu Reaction. Di-p-chlorobenzyl Azodicarboxylate: A New Azodicarboxylate http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2006/8/i22/abs/ol0618757.html
10. (BDP)CuH: A "Hot" Stryker's reagent for Use in Achiral Conjugate Reductions http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2008/10/i02/abs/ol702689v.html
11. Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis-phosphine Ligands http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/2003/125/i29/abs/ja021391f.html
12. Bruce H. Lipshutz, Robert Moretti, Robert Crow "Mixed Higher-order Cyanocuprate-induced Epoxide Openings: 1-Benzyloxy-4-penten-2-ol" Org. Synth. 1990, volume 69, pp. 80.
13. 10.1002/anie.201510570. 26924396. 4966530. Handa Phos: A General Ligand Enabling Sustainable PPM Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature. Angewandte Chemie International Edition. 55. 16. 4914–4918. 2016. Handa. Sachin. Andersson. Martin P.. Gallou. Fabrice. Reilly. John. Lipshutz. Bruce H..
14. 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.
15. 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 .
16. Web site: NSF - OLPA - News Tip: November 29, 2002. www.nsf.gov.
17. 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.