ORGN 21 |
| The iterative synthesis of oligoarenes via the Suzuki-Miyaura coupling has been achieved by using a series of “masked” haloarylboronic acids as building blocks whose ordinarily reactive boronyl groups are temporarily protected by a new masking group derived from 1,8-diaminonaphthalene. The masking group is robust under the coupling reaction conditions using various bases including aqueous NaOH. Treatment of the coupling products having masked boronyl groups with aqueous acid results in quantitative recovery of the unmasked organoboronic acids. By repetition of these steps, i.e., coupling and unmasking steps, oligoarene derivatives are synthesized. The masking strategy can be applied to selective protection of one of the two boronyl groups of benzenediboronic acid derivatives in the Suzuki-Miyaura coupling with haloarenes, leading to the synthesis of oligoarene derivatives bearing terminal boronyl groups.
|
|
Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
