Publications: Recent Chemistry Publications, Safety Publications, Previous Publications
Recent Chemistry Publications
Sedef Karabiyikoglu, Byron A. Boon, and Craig A. Merlic. “Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Alkynes: The Transannular Pauson–Khand Reaction.” J. Org. Chem., 2017, 82 (15), pp 7732–7744. DOI: 10.1021/acs.joc.7b01369
Byron A. Boon, Aaron G. Green, Peng Liu, K. N. Houk, and Craig A. Merlic. “Using Ring Strain to Control 4 pi-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes.” J. Org. Chem., 2017, 82 (9), pp 4613–4624. DOI: 10.1021/acs.joc.7b00203
Cyndi Qixin He, Tiffany Q. Chen, Ashay Patel, Sedef Karabiyikoglu, Craig A. Merlic, and K. N. Houk. “Distortion, Tether, and Entropy Effects on Transannular Diels-Alder Cycloaddition Reactions of 10-18-Membered Rings.” J. Org. Chem., 2015, 80 (21), pp 11039–11047. DOI: 10.1021/acs.joc.5b02288
Karabiyikoglu, Sedef; Iafe, Robert G.; Merlic, Craig A. “Ring-Closing Metathesis with Vicinal Dibromoalkenes as Protected Alkynes: A Synthetic Approach to Macrocyclic Enynes.” Org. Lett., 2015, 17 (21), pp 5248–5251. DOI: 10.1021/acs.orglett.5b02595
Karabiyikoglu, Sedef; Merlic, Craig A. “Transannular [4+2] Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Dienynes.” Org. Lett., 2015, 17 (16), pp 4086–4089. DOI:10.1021/acs.orglett.5b01984
Green, Aaron G.; Liu, Peng; Merlic, Craig A.; and K. N. Houk. “Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C-H Borylation of Substituted Arenes and 5-Membered Heterocycles.” J. Am. Chem. Soc., 2014, 136 (12), pp 4575–4583. DOI: 10.1021/ja411699u
Iafe, R. G.; Kuo, J. L.; Hochstatter, D. G.; Saga, T. S.; Turner, J. W.; Merlic, C. A. “Increasing the Efficiency of the Transannular Diels-Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations” Org. Lett., 2013, 15, 582-585. DOI: 10.1021/ol303394t.
Iafe, R. G.; Chan, D. G.; Kuo, J. L.; Boon, B. A.; Faizi, D. J.; Saga, T. S.; Turner, J. W.; Merlic, C. A. “Cyclization Strategies to Polyenes Using Pd(II)-Catalyzed Couplings of Pinacol Vinylboronates” Org. Lett., 2012, 14, 4282-4285. DOI: 10.1021/ol303394t
Chan, D. G.; Winternheimer, D. J.; Merlic, C. A. “Enol Silyl Ethers via Copper(II)-Catalyzed C-O Bond Formation” Org. Lett., 2011, 13, 2778-2781. DOI: 10.1021/ol2009297
Winternheimer, D. J.; Shade, R. E.; Merlic, C. A. “Methods for Vinyl Ether Synthesis” Synthesis, 2010, 42, 2497-2511. DOI: 10.1055/s-0030-1258166.
Winternheimer, D. J.; Merlic, C. A. “Alkoxydienes via Copper Promoted Couplings: Utilizing an Alkyne Effect” Org. Lett., 2010, 12, 2508-2510. DOI: 10.1021/ol100707s.
Shade, R. E.; Hyde, A. M.; Olsen, J.-C.; Merlic, C. A. “Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers” J. Am. Chem. Soc., 2010, 132, 1202-1203. DOI: 10.1021/ja907982w
Safety Publications
8. Schroeder, I.; Czornyj, E.; Blayney, M. B.; Wayne, N. L.; Merlic, C. A. “Proceedings of the 2018 Laboratory Safety Workshop: Hazard & Risk Management in the Laboratory” ACS Chem. Health Safety 2020, 27(2), 96-104. https://pubs.acs.org/doi/abs/10.1021/acs.chas.0c00012
7. Svenningsen, G. S.; Williams, B.; Blayney, M. B.; Czornyj, E.; Schroeder, I.; Merlic, C. A. “Lessons Learned – Fluoride Exposure” ACS Chem. Health Safety 2020, 27(1), 40-42. https://pubs.acs.org/doi/pdf/10.1021/acs.chas.9b00015
6. Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Lessons Learned – Vacuum Pump Fire” J. Chem. Health Safety 2019, 26(6), 2. https://www.sciencedirect.com/science/article/abs/pii/S1871553219300404?via%3Dihub
5. Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Lessons Learned – Mercury Thermometer Incident” J. Chem. Health Safety 2019, 26(4), 6-8. https://www.sciencedirect.com/science/article/abs/pii/S1871553219300398?via%3Dihub
4. Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Organic Peroxide Incident” J. Chem. Health Safety 2019, 26(3), 3-4. https://www.sciencedirect.com/science/article/abs/pii/S1871553219300234?via%3Dihub
3. Czornyj, E.; Newcomer, D.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Proceedings of the 2016 Workshop Safety By Design – Improving Safety in Research Laboratories” J. Chem. Health Safety 2018, 25(4), 36-49. https://pubs.acs.org/doi/10.1021/acs.chas.8b25409
2. Merlic, C.; Ngai, E.; Schroeder, I.; Smith, K. “Report to the University of Hawaii at Manoa on the Hydrogen/Oxygen Explosion of March 16, 2016. Report 2: Recommendations for Improvements in UH Laboratory Safety Programs” UC Center for Laboratory Safety, 2016. http://cls.ucla.edu/images/
1. Merlic, C.; Ngai, E.; Schroeder, L.; Smith, K. “Report to the University of Hawaii at Manoa on the Hydrogen/Oxygen Explosion of March 16, 2016. Report 1: Technical Analysis of Accident” UC Center for Laboratory Safety, 2016. http://cls.ucla.edu/images/
Previous Publications
60. Garcia, Y.; Schoenebeck, F.; Legault, C. Y.; Merlic, C. A.; Houk, K. N. “Theoretical Bond Dissociation Energies of Halo-Heterocycles: Trends and Relationships to Regioselectivity in Palladium-Catalyzed Cross Coupling Reactions” J. Am. Chem. Soc., 2009, 131, 6632-6639. [link]
59. Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. “Origin of Regioselectivity in Palladium Catalyzed Cross-Coupling Reactions of Heterocycles” J. Am. Chem. Soc., 2007, 129, 12664-12665. [link]
58. Yu, W.; Zhang, F.; Zamborszky, F.; Alavi, B.; Baur, A.; Merlic, C. A.; Brown, S. E. “Electron-Lattice Coupling and Broken Symmetries of the Molecular Salt (TMTTF)2SbF6” Physical Review B. 2004, 70 (12), 121101-1—121101-4. [link]
57. Hietbrink, B. N.; Tantillo, D. J.; Houk, K. N.; Merlic, C. A. “Chromium Tricarbonyl Coordinated Carbocations” In Carbocation Chemistry; Olah, G. A; Prakash, G. K. S., Eds.; Wiley: New York, 2004; Chapter 10, pp. 279-290. [BOOK CHAPTER] [link]
56. Yu, W.; Zamborszky, F.; Alavi, B.; Baur, A.; Merlic, C. A.; Brown, S. E. “Influence of charge order on the ground states of TMTTF molecular salts” Journal de Physique IV 2004, 114, 35-40. [link]
55. Shelkovnikov, S.; Merlic, C. A.; Gonick, H. C. “Influence of Nitric Oxide Donors and Peroxynitrite on the Contractile Effect and Concentration of Norepinephrine” Life Sciences, 2004, 74, 2919-2928. [link]
54. Lima, M. A.; Barbosa-Filho, J. M.; Merlic, C. A.; Doroh, B. C.; Maia, J. G. S.; Silva, M. S.; da-Cunha, E. V. L. “Alkaloids and volatile constituents from Guatteria poepigiana” Biochemical Systematics and Ecology 2004, 32, 347-349. [link]
53. Merlic, C. A.; Doroh, B. C. “Amine Catalyzed Coupling of Aldehydes and Ketenes Derived from Fischer Carbene Complexes: Formation of b-Lactones and Enol Ethers” J. Org. Chem. 2003, 68, 6056-6059. [link]
52. Merlic, C. A.; Zechman, A. L. “Selectivity in Rhodium(II) Catalyzed Reactions of Diazo Compounds: Effects of Catalyst Electrophilicity, Diazo Substitution, and Substrate Substitution. From Chemoselectivity to Enantioselectivity” Synthesis 2003, 1137-1156. [REVIEW] [link]
51. Zamborszky, F.; Yu, W.; Raas, W.; Brown, S. E.; Alavi, B.; Merlic, C. A.; Baur, A.; Lefebvre, S.; Wzietek, P.; “Influence of Charge Order on the Ground State of TMTTF Conductors” Journal de Physique IV 2002, 12, 139-144.
50. Zamborszky, F.; Yu, W.; Raas, W.; Brown, S. E.; Alavi, B.; Merlic, C. A.; Baur, A.; “Competition and Coexistence of Bond and Charge Orders in (TMTTF)2AsF6” Physical Review B. 2002, 66 (8), 081103-1—081103-4.
49. Merlic, C. A.; Zechman, A. L.; Miller, M.; “Reactivity of (h6-Arene)tricarbonylchromium Complexes with Carbenoids: Arene Activation or Protection?” J. Am. Chem. Soc. 2001, 123, 11101-11102. [link]
48. Merlic, C. A.; Hietbrink, B. N.; Houk, K. N.; “Donor and Acceptor Properties of the Chromium Tricarbonyl Substituent in Benzylic and Homobenzylic Anions, Cations, and Radicals” J. Org. Chem. 2001, 66, 6738-6744. [link]
47. Merlic, C. A.; You, Y.; McInnes, D. M.; Zechman, A. L.; Miller, M. M.; Deng, Q. “Benzannulation Reactions of Fischer Carbene Complexes for the Synthesis of Indolocarbazoles” Tetrahedron 2001, 57, 5199-5212. [link]
46. Merlic, C. A.; Miller, M.; Hietbrink, B. N.; Houk, K. N.; “Reactivity of (h6-Arene)tricarbonylchromiumComplexes Toward Additions of Anions, Cations, and Radicals” J. Am. Chem. Soc. 2001, 123, 4904-4918. [link]
45. Merlic, C. A.; Walsh, J. “The Tricarbonylchromium Template for Stereocontrol in Radical Reactions of Arenes” J. Org. Chem. 2001, 66, 2265-2274. [link]
44. Merlic, C. A.; Aldrich, C. C. Albaneze-Walker, J.; Saghatelian, A.; Mammen, J. “Total Synthesis of the Calphostins: Application of Fischer Carbene Complexes and Thermodynamic Control of Atropisomers” J. Org. Chem. 2001, 66, 1297-1309. [link]
43. Merlic, C. A.; Miller, M. “Neighboring Group Participation by Chromium in Substitution Reactions of (h6-Arene)tricarbonylchromium Complexes” Organometallics 2001, 20, 373-375. [link]
42. Merlic, C. A.; Fam, B. C.; Miller, M. M. “WebSpectra: Online NMR and IR Spectra for Students” J. Chem. Ed. 2001, 78, 118-120. [link]
41. Chow, D. S.; Zamborszky, F.; Alavi, B.; Tantillo, D. J.; Baur, A.; Merlic, C. A.; Brown, S. E. “Charge Ordering in the TMTTF Family of Molecular Conductors” Phys. Rev. Lett. 2000, 85, 1698-1701. [link]
40. Merlic, C. A.; Baur, A.; Aldrich, C. C. “Acylamino Chromium Carbene Complexes: Direct Carbonyl Insertion, Formation of Münchnones and Trapping with Dipolarophiles”J. Am. Chem. Soc. 2000, 122, 7398-7399. [link]
39. Tantillo, D. J.; Hietbrink, B. N.; Merlic, C. A.; Houk, K. N. “Attenuating and Supplanting Nonclassical Stabilization: Cr(CO)3-Complexed Benzonorbornenyl Cations” J. Am. Chem. Soc. 2000, 122, 7136-7137. [link]
38. Merlic, C. A.; Baur, A.; Yamada, K.; Brown, S. E. “Synthesis of Quadruply Carbon-13 Labeled Tetramethyltetrathiafulvalene ” Syn. Commun. 2000, 30, 2677-2685. [link]
37. Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J.; Saghatelian, A. “Carbene Complexes in the Synthesis of Complex Natural Products: Total Synthesis of the Calphostins” J. Am. Chem. Soc. 2000, 122, 3224-3225. [link]
36. Chow, D. S.; Brown, S. E.; Wzietek, P.; Fogliatti, D.; Alavi, B.; Merlic, C. “Singular Behavior in the Pressure-Tuned Competition Between Spin-Peierls and Antiferromagnetic Ground States of (TMTTF)2PF6” Synthetic Metals 1999, 103, 2058-2059. [link]
35. Brown, S. E.; Clark, W. G.; Alavi, B.; Chow, D. S.; Merlic, C. A.; Tantillo, D.J. “Incommensurate Phase of the Organic Spin-Peierls Compound (TMTTF)2PF6” Synthetic Metals, 1999, 103, 2056-2057. [link]
34. Merlic, C. A.; Baur, A.; Tantillo, D. J.; Brown, S. E. “Synthesis of Carbon-13 Labeled Tetramethyltetrathiafulvalene” Syn. Commun. 1999, 29, 2953-2958. [link]
33. Brown, S. E.; Clark, W. G.; Alavi, B.; Hall, D.; Naughton, M. J.; Tantillo, D. J.; Merlic, C. A. “High- Field Magnetization of the Spin-Peierls Compound (TMTTF)2PF6” Phys. Rev. B 1999, 60, 6270-6272.
32. Merlic, C. A.; Walsh, J. C.; Tantillo, D. J.; Houk, K. N. “Chemical Hermaphroditism: The Potential of the Cr(CO)3 Moiety to Stabilize Transition States and Intermediates with Anionic, Cationic, or Radical Character at the Benzylic Position” J. Am. Chem. Soc. 1999, 121, 3596-3606. [link]
31. Chow, D. S.; Wzietek, P.; Fogliatti, D.; Alavi, B.; Tantillo, D. J.; Merlic, C. A.; Brown, S. E “Singular Behavior in the Pressure-Tuned Competition Between Spin-Peierls and Antiferromagnetic States of (TMTTF)2PF6” Phys. Rev. Lett. 1998, 81, 3984-3987.[link]
30. Brown, S. E.; Clark, W. G.; Zamborszky, F.; Klemme, B. J.; Kriza, G.; Alavi, B.; Merlic, C. A.; Tantillo, D. J.; Kuhns, P.; Moulton, W. “13C NMR Measurements of the High-Magnetic Field, Low-temperature Phases of (TMTTF)2PF6” Phys. Rev. Lett. 1998, 80, 5429-5432. [link]
29. Merlic, C. A.; Walsh, J. C. “Completely Diastereoselective Radical Reactions Using Arenechromium Tricarbonyl Complexes” Tetrahedron Lett. 1998, 39, 2083-2086. [link]
28. Merlic, C. A.; Wu, F. “Synthesis of b-Keto Fischer Carbene Complexes” Journal of Organometallic Chemistry 1998, 553, 183-191. [link]
27. Zwick, F.; Brown, S.; Margaritondo, G.; Merlic, C.; Onellion, M.; Voit, J.; Grion, M. “Absence of Quasiparticles in the Photoemission Spectra of Quasi-One-Dimensional Bechgaard Salts” Phys. Rev. Lett. 1997, 79, 3982-3985. [link]
26. Merlic, C. A.; McInnes, D. M. “Synthesis of Indolocarbazoles via Sequential Palladium Catalyzed Cross Coupling and Benzannulation Reactions” Tetrahedron Lett. 1997, 38, 7661-7664. [link]
25. Merlic, C. A.; McInnes, D. M.; You, Y. “Synthesis of Indolocarbazoles via Annulations of Chromium Carbene Complexes” Tetrahedron Lett. 1997, 38, 6787-6790. [link]
24. Merlic, C. A.; Walker, M. J. “Virtual Office Hours: Facilitating Faculty-Student Communication” Int. J. Educ. Telecommun. 1997, 3, 261-278.
23. Merlic, C. A.; Pauly, M. E. “Ruthenium-Catalyzed Cyclizations of Dienylalkynes Via Vinylidene Intermediates” J. Am. Chem. Soc. 1996, 118, 11319-11320. [link]
22. Merlic, C. A.; Walker, M. J. “Virtual Office Hours: A Communication Tool for Students and Teachers” WebNet 96 World Conference of the Web Society Preceedings, Maurer, Ed., 1996, Association for the Advancement of Computing in Education, pp 360-365.
21. Merlic, C. A.; Motamed, S.; Quinn, B. “Structure Determination and Synthesis of Fluoro Nissl Green: An RNA Binding Fluorochrome” J. Org. Chem. 1995, 60, 3365-3369. [link]
20. Merlic, C. A.; Albaneze, J. “Synthesis of Alkoxy-Substituted Allenyl- and Propargylstannane Reagents from Carbene Complexes” Tetrahedron Lett. 1995, 36, 1011-1014. [link]
19. Merlic, C. A.; Albaneze, J. “Rapid Synthesis of Functionalized, Alkoxy-Substituted, Allylstannanes from Carbene Complexes” Tetrahedron Lett. 1995, 36, 1007-1010. [link]
18. Quinn, B; Toga, A.; Motamed, S.; Merlic, C. A.. “Fluoro Nissl Green: A Novel Fluorescent Counterstain for Neuroanatomy” Neuroscience Lett. 1995, 184, 169-172. [link]
17. Merlic, C. A.; Bendorf, H. D. “Cyclopropanation of C60 Via a Fischer Carbene Complex” Tetrahedron Lett. 1994, 35, 9529-9532. [link]
16. Merlic, C. A. “2-Hydroxy-1-methoxy-furo[2,3-b]naphthalene” In Photochemical Key Steps in Organic Synthesis; Mattay, J.; Griesbeck, A., Eds.; VCH: Weinheim, Germany, 1994, pp 271-273.
15. Merlic, C. A.; Roberts, W. M. “Regioselectivity of Photochemical Annulations of Chromium Carbene Complexes” Tetrahedron Lett. 1993, 34, 7379-7382. [link]
14. Merlic, C. A.; Burns, E. E. “Chemoselectivity in the Isonitrile Metathesis Route to Aromatic Amines” Tetrahedron Lett. 1993, 34, 5401-5404. [link]
13. Merlic, C. A.; Bendorf, H. D. “Titanium-Templated [4+2] Oxidative Cycloadditions: A Facile Route to 7-Hydroxynorbornenes”Organometallics 1993, 12, 559-564. [link]
12. Merlic, C. A.; Xu, D; Gladstone, B. “Aminobenzannulation Via Photocyclization Reactions of Chromium Dienyl(Amino)carbene Complexes. Synthesis of Ortho Amino Aromatic Alcohols” J. Org. Chem. 1993, 58, 538-545. [link]
11. Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. ” Stereochemistry of Intermolecular Radical Reactions of Unsaturated Tungsten Carbene Complexes,” Tetrahedron Lett. 1993, 34, 227-230. [link]
10. Merlic, C. A.; Burns, E. E.; Xu, D.; Chen, S. Y. “Aminobenzannulation Via Metathesis of Isonitriles Using Chromium Carbene Complexes” J. Am. Chem. Soc. 1992, 114, 8722-8724. [link]
9. Merlic, C. A.; Adams, B. “Molybdenum-95 Nuclear Magnetic Resonance Studies on Molybdenum Carbonyl Complexes of Isonitriles and Amines” J. Organomet. Chem. 1992, 431, 313-325. [link]
8. Merlic, C. A.; Xu, D.; Khan, S. I. ” Synthesis, Structure and Reactivity of Cyclic Arene Chromium Carbene Complexes” Organometallics 1992, 11, 412-418. [link]
7. Merlic, C.A.; Xu, D. “Intermolecular Radical Reactions of Unsaturated Chromium and Tungsten Carbene Complexes,” J. Am. Chem. Soc. 1991, 113, 9855-9856. [link]
6. Merlic, C.A.; Xu, D. “Cyclization Reactions of Dienyl Chromium Carbene Complexes. Entry to Ortho Substituted Aromatic Alcohols via a Designed Photoreaction” J. Am. Chem. Soc. 1991, 113, 7418-7420. [link]
5. Merlic, C.A.; Semmelhack, M.F. “An Interesting Chloride Ion Effect in the Heck Reaction,” J. Organomet. Chem. 1990, 391, C23-C27. [link]
4. Trost, B.M.; Merlic, C.A. “Ligand Dependence of Molybdenum Catalyzed Alkylations. Molybdenum Isonitrile Complexes as a New Class of Highly Reactive Alkylation Catalysts,” J. Am. Chem. Soc. 1990, 112, 9590-9600. [link]
3. Trost, B.M.; Merlic, C.A. “Geminal Alkylation – Substitutions of Allyl Sulfones. Regiocontrol via Molybdenum Catalysis,” J. Org. Chem. 1990, 55, 1127-1129. [link]
2. Trost, B.M.; Merlic, C.A. “Diastereoselectivity Control Elements. Acyclic Diastereocontrol in Formation and Reactions of g-hydroxysulfones,” J. Am. Chem. Soc. 1988, 110, 5216-5218. [link]
1. Little, R.D.; Losinski-Dang, L.; Venegas, M.G.; Merlic, C.A. “Some Unusual Reactions of Molecular Oxygen with Bicyclic Diazenes which Typically Serve as Precursors to Alkylidenecyclopentane-1,3-diyls; Peroxide Formation,” Tetrahedron Lett. 1983, 24, 4499-4502. [link]