ORGN 892 |
| The classical Scholl reaction (ca. 1885) has been around more than 100 years in one form or another, yet this methodology still offers the opportunity to uncover many intriguing and useful secrets for the synthesis of organic hydrocarbon materials (for historical perspective see E. Clar ). In recent years, there has been an enormous resurgence in the synthesis of new aromatic hydrocarbons for organic electronics applications (e.g., OTFT, OLED, photovoltaics, organic metals, etc.). Much of this new work has made excellent and creative use of metal-mediated coupling chemistries (Ullman reactions ) for the construction of desired carbon-carbon bond frameworks. The advantages to this strategy are obvious (i.e., chemoselectivity), however, there are also a number of disadvantages that have received little attention. First, aromatic halogen bonds are widely considered to be problematic impurities when present in organic electronics applications. Second, additional synthetic steps are typically required to access “activated” hydrocarbons suitable for Ullman reactions. In some cases, one may avoid both of these problems by returning to the classical radical cation chemistries of the Scholl reaction. Below is shown one generic example of such a sequence. This paper will describe several others that have recently been explored.
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New Reactions and Methodology
8:00 AM-11:40 AM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
