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[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

Department of Chemistry and Biochemistry, UCSB: People, Faculty
Past Award Entries and Recipients | Green Chemistry | US EPA
Zymes llc Archived July 17, 2008, at the Wayback Machine
TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature
Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group
Simplification of the Mitsunobu Reaction. Di-p-chlorobenzyl Azodicarboxylate: A New Azodicarboxylate
(BDP)CuH: A "Hot" Stryker's reagent for Use in Achiral Conjugate Reductions
Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis-phosphine Ligands
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.
https://pubs.rsc.org/en/Content/ArticleLanding/2018/GC/C8GC01356J#!divAbstract. Cite journal requires |journal= (help); Missing or empty |title= (help)
https://www.sigmaaldrich.com/ifb/acta/v41/acta-vol41-2008.html#73/z
https://www.nsf.gov/od/lpa/news/02/tip021129.htm
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.

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[1] Department of Chemistry and Biochemistry, UCSB: People, Faculty

[2] Past Award Entries and Recipients | Green Chemistry | US EPA

[3] Zymes llc Archived July 17, 2008, at the Wayback Machine

[4] TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature

[5] “Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

[6] Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water

[7] HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature

[8] β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group

[9] Simplification of the Mitsunobu Reaction. Di-p-chlorobenzyl Azodicarboxylate: A New Azodicarboxylate

[10] (BDP)CuH: A "Hot" Stryker's reagent for Use in Achiral Conjugate Reductions

[11] Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis-phosphine Ligands

[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. {{DOI:10.15227/orgsyn.069.0080}}

[13] 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.

[14] ttps://pubs.rsc.org/en/Content/ArticleLanding/2018/GC/C8GC01356J#!divAbstract. Cite journal requires |journal= (help); Missing or empty |title= (help)

[15] ttps://www.sigmaaldrich.com/ifb/acta/v41/acta-vol41-2008.html#73/z

[16] ttps://www.nsf.gov/od/lpa/news/02/tip021129.htm

[17] 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.