个人简介

Bruce Lipshutz has been at UC Santa Barbara since joining the faculty as an Assistant Professor in 1979. Much of his career has been focused on developing new reagents and technologies that have broad appeal in the synthetic community, many of which are now, or will soon be, commercially available (e.g., SEM-Cl, “Higher Order Cuprates”, “Cuprate-in-a-Bottle”, DCAD, “Copper Hydride-in-a-Bottle”, Ni/C, Cu/C, PTS, TPGS-750-M, etc.). The group’s efforts have, in part, shifted with an emphasis on “green chemistry”. Thus, there is ongoing development of a mix of methods in heterogeneous catalysis, including newly developed mixed metal-supported cross-coupling reagents, and homogeneous catalysis. The latter focuses on micellar catalysis to effect transition metal-catalyzed cross-couplings in water at room temperature, with an accent on development of new “designer surfactants.” Also being actively pursued are projects in total or partial synthesis of biaryls that possess axial chirality (e.g., the A-B biaryl section of vancomycin, and the antimalarial korupensamines and related targets), and syntheses associated with, and analogs derived from, coenzyme Q10.

研究领域

Organic & Bioorganic/Molecular Design & Synthesis/Biomedical Sciences/Energy/Catalysis & Green Chemistry

The overriding theme to our programs in organic synthesis is “catalysis.” Areas in which new technologies are being pursued include: • heterogeneous catalysis; new reagents that rely on two forms of carbon as the solid support: charcoal and graphite. Transition metals that are of interest include Pd (“UC Pd”), Ni (Ni/C and Ni/Cg), and Cu (Cu/C). • homogeneous catalysis; new methodologies in asymmetric, ligand-accelerated processes (e.g., asymmetric hydrosilylation with ligated CuH). Catalysis is also playing a key role in our efforts in total synthesis, in particular as applied to axially chiral biaryls that constitute key sections of many natural products (e.g., vancomycin, michellamines, etc.). Nanotechnology is another main thrust of our group’s research, in particular within the domain of green chemistry. In this vein, micellar catalysis can offer a rare opportunity to “get organic solvents out of organic reactions.” To achieve this goal, novel ”designer” surfactants are being developed, each of which is “benign by design” in the Anastas sense (i.e., following the 12 Principles of Green Chemistry). The new methods that have been reported, and those currently under development, include Pd-catalyzed cross-couplings for Heck, Sonogashira, Suzuki-Miyaura, and Negishi reactions. Similar procedures have been discovered that effect aminations, silyations, and borylations, as well as asymmetric CuH-catalyzed hydrosilylations…all done in water at room temperature.

近期论文

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Dehalogenation of Functionalized Alkyl Halides in Water at Room Temperature. N. A. Isley, M. S. Hageman, B. H. Lipshutz, Green Chem., 2015, Advanced Article Article Transitioning Organic Synthesis from Organic Solvents to Water. What's Your E Factor? B. H. Lipshutz, S Ghorai, Green Chem., 16, 3660 Asymmetric Gold-Catalyzed Lactonizations in Water at Room Temperature. S. Handa, D. J. Lippincott, D. H. Aue, B. H. Lipshutz, Angew. Chem., Int. Ed., 53 (40), 10658 A Palladium Nanoparticle-Nanomicelle Combination for the Stereoselective Semihydrogenation of Alkynes in Water at Room Temperature. E. D. Slack, C. M. Gabriel, B. H. Lipshutz, Angew. Chem., Int. Ed., 53 (51), 14051 Stereoretentive Pd-Catalyzed Kumada-Corriu Couplings of Alkenyl Halides at Room Temperature. A. Krasovskiy; S. Haley, K. Voidtritter, B. H. Lipshutz, Org. Lett. 16, 4066 CuH in Asymmetric Reductions, In Copper-Catalyzed Asymmetric Synthesis. B. H. Lipshutz, Wiley-VCH Review Transitioning organic synthesis from organic solvents to water. What’s your E Factor? B. H. Lipshutz, S. Ghorai, Green Chem., 16, 3660 Copper-catalyzed Hydrophosphinations in Water at Room Temperature. N. A. Isley, R. T. Linstadt, E. Slack, B. H. Lipshutz, Dalton Trans., 43, 13196 Aerobic Oxidation in nanomicelles of Aryl Alkynes, in Water at Room Temperature. S. Handa, J. C. Fennewald, B. H. Lipshutz, Angew. Chem., Int. Ed., 53, (13), 3432 Stereoselective Silylcuprations of Conjugated Alkynes in Water at Room Temperature. R. T. H. Linstadt, C. A. Peterson, D. J. Lippincott, C. I. Jette, B. H. Lipshutz, Angew. Chem., Int. Ed., 53 (16), 4159 Selective oxidations of activated alcohols in water at room temperature. B. H. Lipshutz, M. Hageman, J. C. Fennewald, R. Linstadt, E. Slack, K. Voigtritter, Chem. Comm. 50, 11378 Leveraging the Micellar Effect: Gold-Catalyzed Dehydrative Cyclizations…in Water at Room Temperature. S. R. K. Minkler, N. A. Isley, D. J. Lippincott, N. Krause, B. H. Lipshutz, Organic Lett., 16 (3), 724 Copper-catalyzed trifluoromethylation of N-arylacrylamides “on water” at Room Temperature. F. Yang, P. Klumphu, Y-M. Liang, B. H. Lipshutz, Chem. Comm., 50, 936 “Nok”: A Phytosterol-Based Amphiphile Enabling Transition Metal-Catalyzed Couplings in Water at Room Temperature. P. Klumphu, B. H. Lipshutz, J. Org. Chem., 79, 888 Chemoselective Reductions of Nitroaromatics in Water at Room Temperature. S. M. Kelly, B. H. Lipshutz, Organic Lett., 16, 98 Installation of Protected Ammonia Equivalents onto Aromatic and Heteroaromatic Rings in Water Enabled by Micellar Catalysis. N. A. Isley, S. Dobarco, B. H. Lipshutz, Green Chem., 16, 1480 Trifluoromethylations of Heterocycles in Water at Room Temperature. J. C. Fennewald, B. H. Lipshutz, Green Chem., 16, 1097 Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: No Organic Solvents. N. A. Isley, F. Gallou, B. H. Lipshutz, J. Am. Chem. Soc., 135 (47), 17707 Applying the Hydrophobic Effect to Transition Metal-Catalyzed Couplings in Water at Room Temperature, In Transition Metal-Catalyzed Couplings in Process Chemistry. B. H. Lipshutz, Wiley-VCH Review “Click” and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles. B. H. Lipshutz, Z. Boskovic, C. S. Crowe, V. K. Davis, H. C. Whittemore, D. A. Vosburg, and A. G. Wenzel, J. Chem. Ed., 90, 1514 On the Way Towards Greener Transition Metal Catalyzed Processes as Quantified by E Factors