Bruce H. Lipshutz

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 ^{[7] [13]}
• Use of nonionic amphiphiles for transition metal-mediated cross coupling in organic synthesis. ^[14]
• Low-cost synthesis of Coenzyme Q10. ^{[15] [16]}

References

1. "People | Department of Chemistry - UC Santa Barbara". www.chem.ucsb.edu.
2. "Past Award Entries and Recipients | Green Chemistry | US EPA". Archived from the original on August 3, 2012. Retrieved 12 August 2023.
3. "Zymes llc". Archived from the original on July 17, 2008.
4. Lipshutz, Bruce H.; Ghorai, Subir; Abela, Alexander R.; Moser, Ralph; Nishikata, Takashi; Duplais, Christophe; Krasovskiy, Arkady; Gaston, Ricky D.; Gadwood, Robert C. (2011). "TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature". The Journal of Organic Chemistry. 76 (11): 4379–4391. doi:10.1021/jo101974u. PMC   3608414 . PMID   21548658.
5. Klumphu, Piyatida; Lipshutz, Bruce H. (2014). ""Nok": A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature". The Journal of Organic Chemistry. 79 (3): 888–900. doi:10.1021/jo401744b. PMC   4013797 . PMID   24447127.
6. Handa, Sachin; Wang, Ye; Gallou, Fabrice; Lipshutz, Bruce H. (2015). "Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water" . Science. 349 (6252): 1087–1091. Bibcode:2015Sci...349.1087H. doi:10.1126/science.aac6936. PMID   26339028.
7. Handa, Sachin; Andersson, Martin P.; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H. (2016). "HandaPhos: 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. doi:10.1002/anie.201510570. PMC   4966530 . PMID   26924396.
8. Lipshutz, Bruce H.; Pegram, Joseph J. (January 1980). "β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group" . Tetrahedron Letters. 21 (35): 3343–3346. doi:10.1016/S0040-4039(00)78684-9.
9. Lipshutz, Bruce H.; Chung, David W.; Rich, Brian; Corral, Ricardo (2006). "Simplification of the Mitsunobu Reaction. Di- p -chlorobenzyl Azodicarboxylate: A New Azodicarboxylate" . Organic Letters. 8 (22): 5069–5072. doi:10.1021/ol0618757. PMID   17048845.
10. Baker, Benjamin A.; Bošković, Žarko V.; Lipshutz, Bruce H. (2008). "(BDP)CuH: A "Hot" Stryker's Reagent for Use in Achiral Conjugate Reductions" . Organic Letters. 10 (2): 289–292. doi:10.1021/ol702689v. PMID   18092793.
11. Lipshutz, Bruce H.; Noson, Kevin; Chrisman, Will; Lower, Asher (2003). "Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis - phosphine Ligands" . Journal of the American Chemical Society. 125 (29): 8779–8789. Bibcode:2003JAChS.125.8779L. doi:10.1021/ja021391f. PMID   12862472.
12. "Mixed higher-order cyanocuprate-induced epoxide openings: 1-benzyloxy-4-penten-2-ol". Organic Syntheses. 69: 80. 1990. doi:10.15227/orgsyn.069.0080.
13. Landstrom, Evan B.; Handa, Sachin; Aue, Donald H.; Gallou, Fabrice; Lipshutz, Bruce H. (2018). "Evan Phos: A ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water" . Green Chemistry. 20 (15): 3436–3443. doi:10.1039/C8GC01356J.
14. "Merck KGaA". Archived from the original on 2016-11-12. Retrieved 2019-06-16.
15. "NSF - OLPA - News Tip: November 29, 2002". www.nsf.gov.
16. Lipshutz, Bruce H.; Lower, Asher; Berl, Volker; Schein, Karin; Wetterich, Frank (2005). "An Improved Synthesis of the "Miracle Nutrient" Coenzyme Q10". Organic Letters. 7 (19): 4095–4097. doi:10.1021/ol051329y. PMID   16146360.