Bruce H. Lipshutz (born 1951) is an American chemist. He is a professor at the University of California, Santa Barbara.[1]
Biography edit
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 edit
Reagents edit
- 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 edit
- 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]
References edit
- ^ "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.
- ^ TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature [1]
- ^ “Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature [2]
- ^ Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water [3]
- ^ HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature [4]
- ^ β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group [5]
- ^ Simplification of the Mitsunobu Reaction. Di-p-chlorobenzyl Azodicarboxylate: A New Azodicarboxylate [6]
- ^ (BDP)CuH: A "Hot" Stryker's reagent for Use in Achiral Conjugate Reductions [7]
- ^ Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis-phosphine Ligands [8]
- ^ 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. {{DOI:10.15227/orgsyn.069.0080}}
- ^ Handa, Sachin; Andersson, Martin P.; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H. (2016). "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. doi:10.1002/anie.201510570. PMC 4966530. PMID 26924396.
- ^ 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.