Merlic, Craig A.


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Division
Organic
Title
Faculty
Associate Professor
Specialties
Organic
Synthesis

Contact Information

Email
Office
Molecular Sciences Building 3505B
(310) 825-5466
Lab
Molecular Sciences Building 3234
(310) 206-8550

Short Biography

Dr. Merlic received his B.S. from the University of California, Davis and his Ph.D. from the University of Wisconsin, Madison.

Biography

Professor Merlic obtained his B.S. degree in Chemistry from the University of California, Davis in 1982. As a Fannie and John Hertz Foundation Graduate Fellow at the University of Wisconsin, Madison he earned his Ph.D. degree in Organic Chemistry in 1988. He was a National Institutes of Health Postdoctoral Fellow at Princeton University in the Department of Chemistry. He joined the faculty in the Department of Chemistry and Biochemistry at UCLA in 1989. He served as Vice Chair for the Department from 1997 to 2000 and 2004 to 2008. At UCLA, he has received a National Science Foundation Young Investigator Award, a Camille Dreyfus Teacher-Scholar Award, and an Alfred P. Sloan Research Fellowship in addition to several teaching awards.

Professor Merlic's research focuses on applications of transition metal organometallic chemistry to organic synthesis and extends from catalysis to synthesis of new chemotherapeutic agents. He has invented new processes utilizing palladium and ruthenium catalysts, chromium arenes and carbenes, copper promoted coupling reactions, and devised an exceptionally efficient total synthesis of the calphostin family of protein kinase C inhibitors.

He created two award-winning Internet-based educational projects at UCLA. The first system, Virtual Office Hours, came online in 1995 and pioneered student-faculty communication through online question and answer sessions and delivery of instructional materials. The second project, WebSpectra, presents advanced nuclear magnetic resonance and infrared spectral problems in a unique manner and is used worldwide for teaching spectroscopy in organic chemistry.

Research Interest

Our research program encompasses synthetic organic, synthetic organometallic, and physical organometallic chemistry. Research goals include total synthesis of bioactive natural products, discovery of new reactions and catalysts , development of synthetic methods , new techniques for asymmetric synthesis , and determination of reaction mechanisms . The development of new chemistry using organometallic species is a rich and fertile area due to the unique ability of transition metal fragments to impart special reactivity, selectivity, and stability upon bonded organic moieties. Our research draws on these features to address problems in organic synthesis.

Organometallic Radical Reactions for Stereoselective Synthesis

Organometallic radical reactions are being investigated as new methods for carbon-carbon bond formation. By using transition metal fragments to template the reactions of organic moieties, control of chemoselectivity, regiochemistry and stereochemistry in radical cyclizations is feasible. A wide array of organometallic compounds are employed including iron olefin complexes, cobalt alkyne complexes, iron triene complexes, chromium carbene complexes and arene chromium complexes. The later are used for asymmetric synthesis where both enantiomers of a product are available from a single starting enantiomer. Applications of the newly developed methods to the syntheses of biologically active products such as antitumor agents, unnatural sugars, and antibiotics are under investigation.

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Honors & Awards

  • NSF Young Investigator Award
  • Camille Dreyfus Teacher-Scholar Award
  • Princeton University NIH Postdoctoral Fellow
  • Alfred P. Sloan Research Fellowship

 

Publications

[ Selected Publications ]

  • Origin of Regioselectivity in Palladium Catalyzed Cross-Coupling Reactions of Heterocycles Legault,C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc.2007, 129, 12664-12665.
  • Theoretical Bond Dissociation Energies of Halo-Heterocycles: Trends and Relationships to Regioselectivity in Palladium Catalyzed Cross Coupling Reactions Garcia,Y.; Schoenebeck, F.; Legault, C. Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc.2009, 131, 6632-6639.
  • Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers Shade,R. E.; Hyde, A. M.; Olsen, J.-C.; Merlic, C. A. J. Am. Chem. Soc. 2010, 132, 1202-1203.
  • Alkoxydienes via Copper Promoted Couplings: Utilizing an Alkyne Effect Winternheimer, D. J.; Merlic, C. A. Org. Lett. 2010, 12, 2508-2510.
  • Methods for Vinyl Ether Synthesis Winternheimer, D. J.; Shade, R. E.; Merlic, C. A. Synthesis 2010, 42, 2497-2511.
  • Enol Silyl Ethers via Copper(II)-Catalyzed C-O Bond Formation Chan, D. G.; Winternheimer, D. J.; Merlic, C. A. Org. Lett.2011, 13, 2778-2781.
  • Cyclization Strategies to Polyenes Using Pd(II)-Catalyzed Couplings of Pinacol Vinylboronates Iafe,R. G.; Chan, D. G.; Kuo, J. L.; Boon, B. A; Faizi, D. J.; Saga, T.; Turner, J. W.; Merlic, C. A. Org. Lett. 2012, 14, 4282-4285.
  • Increasing the Efficiency of the Transannular Diels-Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations Iafe,R. G.; Kuo, J. L.; Hochstatter, D. G. ; Saga, T.; Turner, J. W.;Merlic, C. A. Org.Lett. 2013, 15, 582-585.
  • Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C–H Borylation of Substituted Arenes and 5-Membered Heterocycles Green,A. G.; Liu, P.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136,4575-4583.