2008年
Efficient Rhodium-Catalyzed installation of unsaturated ester functions onto porphyirins: Site-specific heck-type addition versus conjugate addition
CHEMISTRY-A EUROPEAN JOURNAL
- ,
- ,
- ,
- 巻
- 14
- 号
- 14
- 開始ページ
- 4256
- 終了ページ
- 4262
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.200701943
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
A facile introduction of alpha,beta-or alpha,beta,gamma,delta-unsaturated ester functions onto porphyrins was achieved through rhodium-catalyzed addition of beta-borylporphyrins to acrylate or 2,4-pentadienoate esters. The reaction of meso-borylporphyrins with acrylates exclusively afforded saturated esters by 1,4-conjugate addition under the same re-mode (Heck-type versus conjugate addition) is highly dependent on the reaction site (beta versus meso). This functionalization has a significant impact on the electronic properties of the pi system of porphyrins, which induces a substantial redshift and broadening in the absorption spectra by effective conjugation through the beta positions. The coplanar structure of the unsaturated ester moieties with respect to the porphyrin core has been unambiguously elucidated by X-ray crystallographic analysis.
- リンク情報
- ID情報
-
- DOI : 10.1002/chem.200701943
- ISSN : 0947-6539
- eISSN : 1521-3765
- ORCIDのPut Code : 12623735
- SCOPUS ID : 53549118268
- Web of Science ID : WOS:000256131800014