Bruce H. Lipshutz (born 1951) is an American chemist. He is a professor at the University of California, Santa Barbara.
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. He is Co-founder of Zymes LLC.
Contributions
Reagents
- Aqueous Micellar Catalysis using TPGS-750-M and Nok.
- Sustainable Palladium catalysis.
- 2-(Trimethylsilyl)ethoxymethyl chloride: hydroxyl protecting group, selectively cleaved with fluoride ion under mild conditions.
- Di-(4-chlorobenzyl)azodicarboxylate (DCAD): recyclable and convenient alternative to diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD) in Mitsunobu reaction.
- Ligated copper hydride.
- Heterogeneous catalysts: nickel-on-charcoal, copper-on-charcoal, nickel-in-graphite, copper+nickel-on-charcoal.
Methodologies
- Higher-order organocuprates (Lipshutz cuprates).
- Chiral and achiral conjugate reductions.
- Catalyst development for ppm Pd-catalyzed C-C couplings in water at ambient
- Use of nonionic amphiphiles for transition metal-mediated cross coupling in organic synthesis.
- Low-cost synthesis of Coenzyme Q10.
References
- "People | Department of Chemistry - UC Santa Barbara". www.chem.ucsb.edu.
- "Past Award Entries and Recipients | Green Chemistry | US EPA". Retrieved 12 August 2023.
- "Zymes llc". Archived from the original on July 17, 2008.
- 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.
- 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.
- 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.
- ^ 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.
- 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.
- 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.
- 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.
- 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. doi:10.1021/ja021391f. PMID 12862472.
- "Mixed higher-order cyanocuprate-induced epoxide openings: 1-benzyloxy-4-penten-2-ol". Organic Syntheses. 69: 80. 1990. doi:10.15227/orgsyn.069.0080.
- 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.
- "Merck KGaA". Archived from the original on 2016-11-12. Retrieved 2019-06-16.
- "NSF - OLPA - News Tip: November 29, 2002". www.nsf.gov.
- 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.