Embedded Files
All articles originating from Western are available open-access via Scholarship@Western after a publication embargo.
68. Exploring effects of the π-conjugation length on silole electrochemiluminescent efficiencies. Xiaoli Qin, Liuqing Yang, Darshil Patel, Xin Wang, Kenneth Chu, Jonathan R. Adsetts, Congyang Zhang, Brian L. Pagenkopf* and Zhifeng Ding* SCIENTIA SINICA Chimica 2022, 52, 1737-1746. [link]
67. Correlating Structures to Electrochemiluminescence Efficiencies of Silole Compounds in Coreactant Systems. Xiaoli Qin, Liuqing Yang, Xin Wang, Darshil Patel, Kenneth Chu, Lindsay Kelland, Jonathan Ralph Adsetts, Congyang Zhang, Mark Steven Workentin, Brian L. Pagenkopf and Zhifeng Ding, ChemElectroChem 2022, 9, e202200605. [link]
66. Benzosiloles with Crystallization‐induced Emission Enhancement of Electrochemiluminescence: Synthesis, Electrochemistry, and Crystallography. Liuqing Yang, Donghyun Koo, Jackie Wu, Jonathan M. Wong, Tyler Day, Ruizhong Zhang, Harshana Kolongoda, Kehan Liu, Jian Wang, Zhifeng Ding and Brian L. Pagenkopf, Chemistry—A European Journal 2020, 26, 11715-11721. [link]
65. Synthesis of Hexahydropyridazines by [4+2] Cycloaddition of Donor-Acceptor Cyclobutanes and cis-Diazenes. Jackie Wu, Paul Winiarz, Dhwanish Patel, Johanna de Jong, David Tong, Tristan Chidley, Naresh Vemula and Brian L. Pagenkopf, Organic Letters 2020, 22, 3140-3144. [link]
64. Gram Scale Synthesis of the Co(nmp)2 Catalyst to Prepare trans-2,5-Disubstituted Tetrahydrofurans by the Aerobic Oxidative Cyclization of 4-Pentene-1-ols. Barbora Morra, Nicholas A. Morra, Daniel G. MacDonald and Brian L. Pagenkopf, Synthesis 2020, 52, 847-852. DOI: https://doi.org/10.1055/s-0039-1690730.
63. Synthesis of Functionalized Tetrahydropyridines by SnCl4-mediated [4+2] Cycloaddition between Donor–Acceptor Cyclobutanes and Nitriles. David Tong, Jackie Wu, Nathan Bazinski, Donghyun Koo, Naresh Vemula and Brian L. Pagenkopf, Chem. Eur. J. 2019, 25, 15244-15247. DOI: https://doi.org/10.1002/chem.201903833. [Link]
62. Cycloadditions of Donor-Acceptor Cyclopropanes and Nitriles. Brian L. Pagenkopf and Naresh Vemula, Eur. J. Org. Chem. 2017, 17, 2561–2567. [link]
This invited review article chronicles our group's development and applications of nitrile-cyclopropane cycloadditions and provides an overview of the area. This review has been selected for inclusion in the EJOC 2019 Readers' Choice Virtual Collection.
61. Synthesis and Reactivity of Alkoxy-activated Cyclobutane-1,1-dicarboxylates. Naresh Vemula and Brian L. Pagenkopf, Org. Chem. Front. 2016, 3, 1205-1212. [link]
This invited article is part of themed collection: Celebrating the 75th Birthday of Professor Barry Trost and 2016 Organic Chemistry Frontiers Review-type Articles.
60. Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes. Tristan Chidley, Naresh Vemula, Cheryl A. Carson, Michael A. Kerr and Brian L. Pagenkopf, Org. Lett. 2016, 18, 2922-2925. [link]
59. Oxidative Cyclization of Tertiary Pentenol Derivatives Forming 2,5,5-trisubstituted THF Rings and the Total Synthesis of Cyclocapitelline. Geoffrey A. Phillips, Cory Palmer, Andrew C. Stevens, Mathew L. Piotrowski, Daryl S. R. Dekruyf and Brian L. Pagenkopf, Tetrahedron Lett. 2015, 56, 6052–6055. [link]
57. Synthesis of (+)-Bovidic Acid. Geoffrey A. Phillips, Timothy B. Wright, Andrew C. Stevens, Brian L. Pagenkopf, Can. J. Chem. 2014, 93, 193-198. [link]
This article is part of a Special Issue to celebrate the centennial of the first research article emanating from the Department of Chemistry at the University of Western Ontario. Undergraduates: GAP, TBW. Graduates: GAP, ACS.
56. The [4+2] Cycloaddition of Donor-Acceptor Cyclobutanes and Nitrosoarenes. Naresh Vemula, Andrew C. Stevens, Tyler B. Schon and Brian L. Pagenkopf, Chem. Commun. 2014, 50, 1668-1670. [link]
55. Gram scale synthesis of the C(1)-C(9) fragment of amphidinolide C. Nicholas A. Morra and Brian L. Pagenkopf, Tetrahedron 2013, 69, 8632-8644. [link]
54. BF2OBn∙OEt2: A Novel Lewis Acid and its use in a Regio- and Stereo-selective Opening of Trisubstituted Epoxides and its Application Towards Amphidinolide C and F. Nicholas A. Morra and Brian L. Pagenkopf, Eur. J. Org. Chem. 2013, 756–760. [link]
53. BF3·OEt2 Catalyzed Reaction of Donor-Acceptor Cyclobutanes with Terminal Alkynes: Single Step Access to 2,3-Dihydrooxepines. Ben P. Machin and Brian L. Pagenkopf, Synlett 2011, 2799–2802. [link]
52. The Formal [4+3] Cycloaddition Between Donor-Acceptor Cyclobutanes and Nitrones. Andrew C. Stevens, Cory Palmer and Brian L. Pagenkopf, Org. Lett. 2011, 13, 1528–1531. [link]
51. Gram Scale Synthesis of the C(18)-C(34) Fragment of Amphidinolide C. Nicholas A. Morra and Brian L. Pagenkopf, Org. Lett. 2011, 13, 572–575. [link] [free reprint]
50. Formal [4+2] Cycloaddition of Alkoxy-Substituted Donor-Acceptor Cyclobutanes and Aldehydes Catalyzed by Yb(OTf)3. Mahmoud M. Abd Rabo Moustafa, Andrew C. Stevens, Ben P. Machin and Brian L. Pagenkopf, Org. Lett. 2010, 12, 4736–4738. [link] [free reprint]
49. Ytterbium Triflate Catalyzed Synthesis of Alkoxy-Substituted Donor–Acceptor Cyclobutanes and their Formal [4+2] Cycloaddition with Imines: Stereoselective Synthesis of Piperidines. Mahmoud M. Abd Rabo Moustafa and Brian L. Pagenkopf, Org. Lett. 2010, 12, 4732–4735. [link] [free reprint]
48. Diels-Alder Chemistry of Siloles and their Transformation into Cyclohex-2-ene-1,4-cis-diols. Andrew C. Stevens and Brian L. Pagenkopf, Org. Lett. 2010, 12, 3658–3661. [link] [free reprint]
47. Synthesis of 5-Azaindoles via a Cycloaddition Reaction Between Nitriles and Donor-Acceptor Cyclopropanes. Mahmoud M. Abd Rabo Moustafa and Brian L. Pagenkopf, Org. Lett. 2010, 12, 3168–3171. [link] [free reprint]
46. Improved Yields and Simplified Purification with a Second Generation Cobalt Catalyst for the Oxidative Formation of trans-THF Rings. Cory Palmer, Nicholas A. Morra, Andrew C. Stevens, Barbora Bajtos, Benjamin P. Machin and Brian L. Pagenkopf, Org. Lett. 2009, 11, 5614—5617. [link ]
Accolades in Total Synthesis
Accolades in Total Synthesis
"…the second generation Pagenkopf catalyst carrying nmp ligands afforded consistently better yields than other cobalt species previously used in the literature." - Angew Chem Int Ed 2013 9534
The reaction was, "exquisitely selective and high yielding when using Co(nmp)2 as the catalyst" - Angew Chem Int Ed 2018 13575
#45. Electrochemical and Photovoltaic Properties of Electropolymerized Poly(thienyl-silole)s. Joshua Byers, Paul DiCarmine, Mahmoud M. Abd Rabo Moustafa, Xin Wang, Brian L. Pagenkopf and Oleg Seminikhin. J. Phys. Chem. B 2009, 113, 15715—15723. [link]
44. A General Asymmetric Aldol Reaction of Silyl Ketene Acetals Derived from Simple Esters to Aryl alpha-Ketoesters. Julie Le Engers and Brian L. Pagenkopf, Eur. J. Org. Chem. 2009, 6109—6111. [link]
43. Synthesis of Tetrahydroisoquinocarbazoles via C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters. Barbora Bajtos and Brian L. Pagenkopf, Org. Lett. 2009, 11, 2780–2783. [link]
42. Total Synthesis of (±)-Quebrachamine via [3+2] Cycloaddition and Chloroacetamide Photocyclization. Barbora Bajtos and Brian L. Pagenkopf, Eur. J. Org. Chem. 2009, 1072-1077. [link]
41. Silole Based Acetylenes as Advanced π-conjugated Systems for Optoelectronic Applications. Mahmoud M. Abd Rabo Moustafa and Brian L. Pagenkopf, Comptes rendus Chimie 2009, 12, 359-365. [link]
40. Synthesis and First X-ray Structures of Cobalt(II) and Cobalt(III) Complexes Bearing 2,4-dioxo-alkanoic Acid Dialkylamide Ligands. Jian Wang, Nicholas A. Morra, Hongda Zhao, Jeffrey S. T. Gorman, Vincent Lynch, Robert McDonald, John F. Reichwein and Brian L. Pagenkopf, Can. J. Chem. 2009, 87, 328—334. [link]
#39. Structural Tuning of Silole Electrogenerated Chemiluminescence. Christina Booker, Xin Wang, Samar Haroun, Jigang Zhou, Michael Jennings, Brian L. Pagenkopf and Zhifeng Ding, Angew. Chem., Int. Ed. 2008, 47, 7731-7735. [link]
38. Total Synthesis of (+/–)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3+2] Cyclization. Christian L. Morales and Brian L. Pagenkopf, Org. Lett. 2008, 10, 157—159. [link] [request free electronic reprint ]
#37. New Electropolymerized Poly(thienyl-silole)s for All-Polymer Solar Cells. Paul M. DiCarmine, Xin Wang, Brian L. Pagenkopf and Oleg A. Semenikhin, Electrochem. Commun. 2008, 10, 229-232 . [link]
36. Reduction of Esters to Ethers Utilizing the Powerful Lewis Acid BF2OTf•OEt2. Nicholas A. Morra and Brian L. Pagenkopf, Synthesis 2008, 511-514. [link]
35. Direct Synthesis of 2,5-Dihalosiloles. Nicholas A. Morra and Brian L. Pagenkopf, Org. Syn. 2008, 85, 53-63. [link]
33. C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters. Barbora Bajtos, Ming Yu, Hongda Zhao and Brian L. Pagenkopf, J. Am. Chem. Soc. 2007, 129, 9631-9634. [link] [request free electronic reprint]
32. Reactions of Alanes and Aluminates with Trisubstituted Epoxides. Development of a Stereospecific Alkynylation at the More Hindered Carbon. Hongda Zhao, Darren W. Engers, Christian L. Morales and Brian L. Pagenkopf, Tetrahedron 2007, 63, 8774—8780. [link] This methodology was used by others in a total synthesis (reference 9, link)
31. Synthesis of Indolizines and Benzoindolizines by Annulation of Donor-Acceptor Cyclopropanes with Electron Deficient Pyridines and Quinolines. Nicholas A. Morra, Christian L. Morales, Barbora Bajtos, Xin Wang, Hyosook Jang, Jian Wang, Ming Yu and Brian L. Pagenkopf, Adv. Synth. Catal. 2006, 2385 - 2390. [link]
30. Advances in Lewis Acid Controlled Carbon-Carbon Bond Forming Reactions Enable a Concise and Convergent Total Synthesis of Bullatacin. Hongda Zhao, Jeffrey S. T. Gorman and Brian L. Pagenkopf, Org. Lett. 2006, 8, 4379-4382 . [link][request free electronic reprint ]
#29. Electrochemistry, Spectroscopy, and Electrogenerated Chemiluminescence of Silole-Based Chromophores. Matthew M. Sartin, Andrew J. Boydston, Brian L. Pagenkopf and Allen J. Bard. J. Am. Chem. Soc. 2006, 128, 10163-10170. [link]
28. Recent Developments in Donor-acceptor Cyclopropanes. Ming Yu and Brian L. Pagenkopf, Tetrahedron 2005, 61, 321–347. [link]
26. A New Class of Substituted Aryl Bis(oxazoline) Ligands for Highly Enantioselective Copper-Catalyzed Asymmetric Aldol Addition of Dienolsilane to Pyruvate and Glyoxylate Esters. Julie Cong-Dung Le and Brian L. Pagenkopf, Org. Lett. 2004, 6, 4097 – 4099. [link]
25. A Controlled, Iterative Synthesis of Oligo[(p-phenyleneethynylene)-alt-(2,5-siloleneethynylene)]s. A. J. Boydston, Youshi Yin and Brian L. Pagenkopf, J. Am. Chem. Soc. 2004, 126, 10350 - 10354. [link]
24. Asymmetric Hydrogenation of Ortho-alkoxy Substituted Arylenamides. Julie Cong-Dung Le and Brian L. Pagenkopf, J. Org. Chem. 2004, 69, 4177 - 4180. [link]
#22. Synthesis of 2,2'-Bipyrroles and 2,2'-Thienylpyrroles from Donor-acceptor Cyclopropanes and 2-Cyanoheteroles. Ming Yu, G. Dan Pantos, Jonathan L. Sessler and Brian L. Pagenkopf, Org. Lett. 2004, 6, 1057 – 1059. [link]
21. Synthesis of the C(1) – C(12) Segment of Peloruside A by an alpha-Benzyloxymethyl Ketone Aldol Strategy. Darren W. Engers, Martin J. Bassindale and Brian L. Pagenkopf, Org. Lett. 2004, 6, 663 – 666. [link]
20. Selective Oxidation of Zirconocyclopentenes via Organoboranes. Jeffrey S. T. Gorman, Scott T. Iacono and Brian L. Pagenkopf, Org. Lett. 2004, 6, 67 – 70. [link]
19. A Powerful New Strategy for Diversity-oriented Synthesis of Pyrroles from Donor-acceptor Cyclopropanes and Nitriles. Ming Yu and Brian L. Pagenkopf, Org. Lett. 2003, 5, 5099 – 5101. [link]
18. Allylation of Donor-Acceptor Cyclopropanes. Ming Yu and Brian L. Pagenkopf, Org. Lett. 2003, 5, 4639 – 4640. [link]
16. Formal [3+2] Cycloadditions of Donor-acceptor Cyclopropanes and Nitriles. Ming Yu and Brian L. Pagenkopf, J. Am. Chem. Soc. 2003, 125, 8122 – 8123. [link]
15. Dipodal Ligands from Chiral Spiro[2.4]hepta-4,6-dienes: Solid State Conformational Effects by Tether Substitution in Dipodal CpP Ruthenium(II) Complexes. Jeffrey S. T. Gorman, Vincent Lynch, Brian L. Pagenkopf and Brandon Young, Tetrahedron Lett. 2003, 44, 5435 – 5439. [link]
14. Acetal Formation by Solvolysis of Glucal-Derived Donor-acceptor Cyclopropanes. Ming Yu and Brian L. Pagenkopf, Tetrahedron 2003, 59, 2765 – 2771. [link]
13. New Mixed Phosphonate Esters by Transesterification of Pinacol-phosphonates and their use in Aldehyde and Ketone Coupling Reactions with Non-stabilized Phosphonates. John F. Reichwein and Brian L. Pagenkopf, J. Org. Chem. 2003, 68, 1459 – 14630. [link]
12. A New Horner-Wadsworth-Emmons Type Coupling Reaction Between Non-stabilized β-Hydroxy Phosphonates and Aldehydes or Ketones. John F. Reichwein and Brian L. Pagenkopf, J. Am. Chem. Soc. 2003, 125, 1821 – 1824. [link]
11. The Regioselective Mono-deprotection of 1,3-Dioxa-2,2-(di-tert-butyl)-2-silacyclohexanes with BF3•SMe2. Ming Yu and Brian L. Pagenkopf, J. Org. Chem. 2002, 67, 4553 – 4558. [link]
10. On the Mechanism of the Silicon-tethered Reductive Pauson-Khand Reaction. John F. Reichwein, Scott T. Iacono and Brian L. Pagenkopf, Tetrahedron 2002, 58, 3813 – 3822. [link]
9. Cyclocarbonylation of Silicon Tethered Enynes Derived from Propargylic Alcohols and Vinylsilanes: A New Reductive Pauson-Khand Reaction with a Traceless Tether. John F. Reichwein, Scott T. Iacono, Mittun C. Patel and Brian L. Pagenkopf, Tetrahedron Lett. 2002, 43, 3739 – 3741. [link]
8. Rhodium Catalyzed Regioselective Olefin Hydrophosphorylation. John F. Reichwein, Mittun C. Patel and Brian L. Pagenkopf, Org. Lett. 2001, 3, 4303 – 4306. [link]
7. Intramolecular Cyclopropanation of Glycals: Studies Toward the Synthesis of Canadensolide, Sporothriolide, and Xylovobide. Ming Yu, Vincent Lynch and Brian L. Pagenkopf, Org. Lett. 2001, 3, 2563 – 2566. [link]
# Collaborative Papers
Dr. Pagenkopf’s publications from graduate and postdoctoral studies
6. (Alkylthio)alkynes as Addends in the Co(0) Catalyzed Intramolecular Pauson-Khand Reaction. Substituent Driven Efficiency and Stereoselectivity Enhancements of Annulation. Brian L. Pagenkopf, David B. Belanger, Donogh O'Mahony and Tom Livinghouse,* Synthesis 2000, 1009 – 1019. [link]
5. Asymmetric Catalysis with Transition Metal Fluorides. Brian L. Pagenkopf and Erick M. Carreira,* Chem. Eur. J. 1999, 5, 3437 – 3442. [link]
4. Titanium Fluoride Catalyzed Asymmetric Addition of Trimethylaluminum to Aldehydes. Brian L. Pagenkopf and Erick M. Carreira,* Tetrahedron Lett. 1998, 39, 9593 – 9596. [link]
3. Mechanistic Insights into the Cu-Catalyzed Asymmetric Aldol Reaction: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate. Brian L. Pagenkopf, Jochen Krüger, Aleksandar Stojanovic and Erick M. Carreira,* Angew. Chem., Int. Ed. Engl. 1998, 37, 3124 – 3126. [link]
2. Photochemical Promotion of the Intramolecular Pauson-Khand Reaction. A New Experimental Protocol for Cobalt Catalyzed [2 + 2 + 1] Cycloadditions. Brian L. Pagenkopf and Tom Livinghouse,* J. Am. Chem. Soc. 1996, 118, 2285 – 2286. [link]
1. Substrate Control of Diastereoselectivity in Zirconium(II) Mediated Enyne Cyclizations. Brian L. Pagenkopf, Eric C. Lund and Tom Livinghouse,* Tetrahedron 1995, 51, 4421 – 4438. [link]
Checked Procedures
1. The Catalytic Intramolecular Pauson-Khand Reaction: 2,3,3a,4-Tetrahydro-2[(4-methylbenzene)sulfonyl]-cyclo[C]Pyrrol-5(1h)-one (Cyclopenta[b]pyrrol-5(1H)-one, 2,3,3a,4-tetrahydro-1-[(4-methylphenyl)sulfonyl]-). Mittun C. Patel, Tom Livinghouse and Brian L. Pagenkopf, Org. Syn. 2003, 80, 93 – 103. [link]
# Collaborative papers.
Google Sites
Report abuse