Liming Zhang

Professor

Contact Phone

(805) 893-7392

Office Location

1631E PSB-N

Specialization

Education

Dr. Zhang received his B. S. degree from Nanchang University (1993), his Master degrees in organic chemistry from Nankai University (1996) and the University of Alabama (1998), and his Ph. D. degree from the University of Michigan (2003). He worked as a postdoctoral fellow at the University of Chicago between 2003 and 2005. He started his independent career at the University of Nevada, Reno in 2005 as an assistant professor and joined the Department of Chemistry and Biochemistry at UC Santa Barbara in July, 2009. He is a recipient of the NSF Faculty Early Career Development Award in 2008, Amgen Young Investigator's Award (2008) and the Alfred P. Sloan Research Fellowship (2009).

Research

Research Group Website: http://www.chem.ucsb.edu/~zhang/index.html

Research Objective

Zhang research group is mainly interested in the development of practically useful and novel synthetic methods based on a range of powerful catalytic platforms/systems. The goal is to streamline synthetic transformations and offer unprecedented efficiency in accessing a large array of functional structures. Application of these novel synthetic methods as key transformations in total synthesis of complicated natural products is an integral part of the research program and serves to test these methods in demanding scenarios and offer new venues to study their biological/medicinal properties via analog synthesis.

  • Gold catalysis is the current focus of the group, and several on-going and future directions in this highly contested area are outlined below:
  • Au(I)/Au(III) catalysis: this approach opens a new venue for studying gold catalysis by incorporating a redox process in gold catalysis, similar to various reactions catalyzed by Pd, Ni, Rh, Cu, and etc.
  • Au-catalyzed oxidation of alkynes: this approach allows facile access to ?-oxo gold carbenes from alkynes directly, essentially making C-C triple bonds equivalent to ?-diazo ketones and therefore offering various benefits and advantages.
  • Combination of gold/platinum catalysis with other metal catalysis to render powerful tandem/sequential transformations for the synthesis of highly functional structures.
  • Au-catalyzed efficient synthesis of N-heterocycles via novel designs
  • Au-catalyzed tandem transformations of propargyl carboxylates
  • Natural product total synthesis using Au/Pt catalysis as key step

Publications

Selected Research Publications

Wang, Y.; Liu, L.; Zhang, L. 'Combining Zn Ion Catalysis with Homogeneous Gold Catalysis: An Efficient Annulation Approach to N-Protected Indoles' Chem. Sci. 2013, 4, 739-746 (http://pubs.rsc.org/en/content/articlelanding/2013/sc/c2sc21333h) [NIGMS (R01 GM084254)]

Xiao, Y.; Zhang, L. “Synthesis of Bicyclic Imidazoles via [2 + 3] Cycloaddition between Nitriles and Regioselectively Generated -Imino Gold Carbene Intermediates” Org. Lett. 2012, http://dx.doi.org/10.1021/ol302102h. [NSF CAREER award (CHE-0969157)]

Yan, Z.-Y.; Xiao, Y.; Zhang, L. “A Gold-Catalyzed One-Step Construction of 5-Electron-Withdrawing Group-Substituted 2,3-Dihydro-1H-Pyrrolizines from Linear Enynyl Azides: Azide as the Nitrene Precursor and A Formal Synthesis of 7-methoxymitosene”Angew. Chem., Int. Ed. 2012, 51, 8624-8627 (http://onlinelibrary.wiley.com/doi/10.1002/anie.201203678/abstract)[NSF CAREER award (CHE-0969157)]

He, W.; Xie, L.; Xu, Y.; Xiang, J.; Zhang, L. “Electrophilicity of [Small Alpha]-Oxo Gold Carbene Intermediates: Halogen Abstractions from Halogenated Solvents Leading to the Formation of Chloro/Bromomethyl Ketones” Org. Biomol. Chem. 2012, 10, 3168-3171. (http://dx.doi.org/10.1039/C2OB25235J) [NSF CAREER award (CHE-0969157)]

Liu, L.; Wang, Y.; Zhang, L. “Formal Synthesis of 7-Methoxymitosene and Synthesis of Its Analog Via a Key PtCl2-Catalyzed Cycloisomerization” Org. Lett. 2012, doi: 10.1021/ol301593w (http://pubs.acs.org/doi/full/10.1021/ol301593w) [NIGMS (R01 GM084254)]

Liu, L.; Zhang, L. “Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process” Angew. Chem., Int. Ed. 2012, 51, 7301-7304 (http://onlinelibrary.wiley.com/doi/10.1002/anie.201203303/pdf) [NIGMS (R01 GM084254)]

Wang, Y.; Ji, K.; Lan, S.; Zhang, L. 'Rapid Access to Chroman-3-Ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers' Angew. Chem., Int. Ed. 2012, 51, 1915-1918. (http://dx.doi.org/10.1002/anie.201107561) [NIGMS (R01 GM084254)]

Noey, E. L.; Luo, Y.; Zhang, L.; Houk, K. N. “Mechanism of Gold(I)-Catalyzed Rearrangements of Acetylenic Amine-N-Oxides: Computational Investigations Lead to a New Mechanism Confirmed by Experiment” J. Am. Chem. Soc. 2012, 134, 1078–1084. (http://pubs.acs.org/doi/abs/10.1021/ja208860x) [NIGMS (R01 GM084254)]

Ye, L.; Wang, Y.; Aue, D. H.; Zhang, L. “Experimental and Computational Evidence for Gold Vinylidenes: Generation from Terminal Alkynes via a Bifurcation Pathway and Facile C–H Insertions” J. Am. Chem. Soc. 2012, 134, 31–34. (http://pubs.acs.org/doi/full/10.1021/ja2091992) [NIGMS (R01 GM084254)]

Sun, S.; Knoll, J.; Luo, Y.; Zhang, L. “Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes” Synlett  2012, 23, 54-56. (https://www.thieme-connect.com/ejournals/abstract/10.1055/s-0031-1289567) [NIGMS (R01 GM084254)]

Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. “Umpolung Reactivity of Indole through Gold Catalysis”Angew. Chem., Int. Ed. 2011, 50, 8358-8362. (http://dx.doi.org/10.1002/anie.201103014) [NIGMS (R01 GM084254)]

Wang, Y.; Ye, L.; Zhang, L. “Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes” Chem. Commun. 2011, 47, 7815-7817. (http://dx.doi.org/10.1039/C1CC12212F) [NIGMS (R01 GM084254)]

He, W.; Li, C.; Zhang, L. "An Efficient [2 + 2 + 1] Synthesis of 2,5-Disubstituted Oxazoles via Gold-Catalyzed Intermolecular Alkyne Oxidation" J. Am. Chem. Soc. 2011, 133, 8482-8485. (http:/dx.doi.org/10.1021/ja2029188) Highlighted by Synfacts [NSF CAREER award (CHE-0969157)]

Luo, Y; Zhang, G.; Hwang, E. S.; Wilcoxon, T. A.;  Zhang, L. "Gold-catalyzed regioselective oxidation of terminal allenes: formation of ?-methanesulfonyloxy methyl ketones" Beilstein J. Org. Chem. 2011, 7, 596-600 (invited). (http://dx.doi.org/10.3762/bjoc.7.69) [NSF CAREER award (CHE-0969157)]

Zhang, G.; Luo, Y.; Wang, Y.; Zhang, L. "Combining Gold(I)/Gold(III) Catalysis and CH Functionalization: A Formal Intramolecular [3+2] Annulation towards Tricyclic Indolines and Mechanistic Studies" Angew. Chem. Int. Ed. 2011, 50, 4450-4454. (http://dx.doi.org/10.1002/anie.201100293) Highlighted by Synfacts [NSF CAREER award (CHE-0969157)]

Ye, L.; He, W.; Zhang, L. “Flexible and Stereoselective Synthesis of Azetidine-3-one via A Key Gold-Catalyzed Intermolecular Alkyne Oxidation” Angew. Chem., Int. Ed. 2011, 50, 3236-3239. (http://dx.doi.org/10.1002/anie.201007624) [NIGMS (R01 GM084254)]

Li, C.; Zhang, L. “Gold-Catalyzed Nitrene Transfer to Activated Alkynes: Formation of ?, ?-Unsaturated Amidines” Org. Lett. 2011, 13, 1738-1741. (http://dx.doi.org/10.1021/ol2002607) [NSF CAREER award (CHE-0969157) and NIGMS (R01 GM084254)]

Wang, Y.; Lu, B.; Zhang, L. " The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes" Chem. Commun. accepted.

Lu, B.; Li, C.; Zhang, L. "Gold-Catalyzed Highly Regioselective Oxidation of C-C Triple Bonds under Non-Acidic Conditions: Propargyl Moieties as Masked ?,?-Unsaturated Carbonyls" J. Am. Chem. Soc. 2010, 132, 14070-14072.

Cui, L.; Li, C.; Zhang, L. "A Modular, Efficient, and Stereoselective Synthesis of Substituted Piperidin-4-ols" Angew. Chem. Int. Ed. 2010, accepted.

Ye, L.; He, W.; Zhang, L. "Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols" J. Am. Chem. Soc. 2010, 132, 8550-8551.

Cui, L.; Ye, L.; Zhang, L. "Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5+2] annulation" Chem. Commun. 2010, 46, 3351-3353.

Wang, S.; Zhang, G.; Zhang, L. "Gold-Catalyzed Reaction of Propargylic Carboxylates via an Initial 3,3-Rearrangement" Synlett 2010, 692-706.

Ye, L.; Cui, L.; Zhang, G.; Zhang, L. "Alkynes as Equivalents of ?-Diazo Ketones in Generating ?-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones" J. Am. Chem. Soc. 2010, 132, 3258-3259.

Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. "Homogeneous Gold-Catalyzed Oxidative Carboheterofunctionalization of Alkenes" J. Am. Chem. Soc. 2010, 132, 1474-1475.

Cao, S.; Zhang, L. "One-Pot Synthesis of Arene-Fused 2-Acylcyclohexenones from Propargylic Carboxylates" Sci. China. Ser. B. Chem. 2009, 52, 1337-1344.

Ye, L.; Zhang. L. "Practical Synthesis of Linear ?-Iodo/Bromo-?, ?-unsaturated aldehydes/ketones from Propargylic Alcohols via Au/Mo Bimetallic Catalysis" Org. Lett. 2009, 11, 3646-3649.

Cui, L.; Peng, Y.; Zhang, L. "A Two-Step, Formal [4 + 2] Approach toward Piperidin-4-ones via Au Catalysis" J. Am. Chem. Soc. 2009, 131, 8394-8395.

Peng, Y.; Cui, L.; Zhang, G.; Zhang, L. "Gold-Catalyzed Homogeneous Oxidative C-O Bond Formation: Efficient Synthesis of 1-Benzoxyvinyl Ketones" J. Am. Chem. Soc. 2009, 131, 5062-5063.

Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. "Gold-Catalyzed Homogeneous Oxidative Cross -Coupling Reactions" Angew. Chem. Int. Ed. 2009, 48, 3112-3115. Highlighted by Nature Chemistry (http://www.nature.com/nchem/reshigh/2009/0409/full/nchem.211.html)

Cui, L.; Zhang, G.; Peng, Y.; Zhang, L. " Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines" Org. Lett. 2009, 11, 1225-1228.