Current Research interests
The research which I and my students undertake is in the area of radical-based synthetic organic chemistry. In the course of this research, we hope to discover new pathways by which organic molecules (consisting primarily, but not entirely, of Carbon and Hydrogen) can react. Much of this work has culminated in publications and presentations at scientific meetings with Middlebury students as coauthors. Since my arrival at Middlebury College, over 60 Middlebury students have participated in my research program for periods of time ranging from one winter term or summer to a full year, or more. Check here for a list of former and present research students, and what I know of their postgraduate careers. Our research has been funded from a variety of sources, most notably the National Science Foundation, Petroleum Research Fund, The Research Corporation, and Vermont-EPSCOR.
Several years ago, I and my students discovered the first examples of radical atom-transfer reactions involving transfer of a phenylseleno group.
We have continued to be interested in the development and use of phenyl selenide and iodine transfer radical reactions as tools for the synthesis of compounds of medicinal interest.
More recently, we have applied atom-transfer methodology to the problem of radical aromatic substitution. Taking this approach, we have developed new methodology for the synthesis of 2-substituted pyrroles and indoles in high yield under non-oxidizing conditions.
Interest in radicals continues to be the major focus of research in my laboratories. We are currently studying ways in which common metal templates for polyenes can modify subsequent radical reactions.
Recent Publications
“The Radical Addition of Dimethyl 2-Ethynylcyclopropane-1,1-dicarboxylate to Electron-Rich Olefins” Byers, J. H.; Goff, P. H.*; Janson, N. J.*; Mazzotta, M. G.*; Swigor, J. E. Synthetic Communications, 2006, in press.
“Radical Additions to (n6-Styrene) Chromium Tricarbonyl” Byers, J. H.; Janson, N. J.* Organic Letters, 2006, 8, 3453.
“Thiocarbonyldiimidazole” Byers, J.H. Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed. Wiley, 2006, in press.
“Radical Reactions Mediated by Cyclobutadieneiron Tricarbonyl” Byers, J. H.; Sontum, S. F.; Dimitrova, T. S.*; Huque, S.*; Zhang, Y.*; Zegarelli, B. M.*; Jasinski, J. P; Butcher, R. P. Organometallics 2006, 25, 3787.
"Tandem Radical-Electrophilic Annulations to Pyrrole" Byers, J. H.; DeWitt, A.*; Nasveschuk, C. G.*; Swigor, J. E. Tetrahedron Lett., 2004, 45, 6587-6590.
"A One-step Radical Synthesis of Pyrrol-2-Acetic Acids" Byers, J. H.; Duff, M. P.*; Woo, G. W.*, Tetrahedron Lett., 2003, 44, 6853-6855 .
"Syntheses of 3-Acylindoles via the Alkylation of the Dianion of 3-Acetylindole" Byers, J. H.; Zhang, Y.* Heterocycles, 2002, 57, 1293-1297.
Recent Grants
$200,000 from NSF-MRI for “Acquisition of an LC/MS System” 2005
$24,900 from Vermont-EPSCOR for “Purchase of a solvent purification system” 1/05
$5000 from Pfizer Pharmaceuticals Central Research in support of an undergraduate summer research assistant, 4/04
$300,000 from the NSF-RUI for “Transition Metal Templated Radical Reactions” 7/03-6/06.
$8900 from Vermont-EPSCOR for “Radical Chemistry of Cyclobutadiene Iron Tricarbonyl” 6/03-8/03.