2017年5月31日
Synthesis and Catalytic Applications of a Triptycene-Based Monophosphine Ligand for Palladium-Mediated Organic Transformations.
ACS omega
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- 巻
- 2
- 号
- 5
- 開始ページ
- 1930
- 終了ページ
- 1937
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/acsomega.7b00200
- 出版者・発行元
- AMER CHEMICAL SOC
1-Methoxy-8-(diphenylphosphino)triptycene (1), featuring high structural rigidity and steric bulkiness around the phosphine functionality, was synthesized as a new chiral monophosphine ligand for transition metal-catalyzed reactions. In the presence of 5-10 mol ppm (i.e., 0.0005-0.001 mol %) Pd(OAc)2 and 1 (2 equiv for Pd), Suzuki-Miyaura cross-coupling reactions of aryl bromides and arylboronic acids proceeded effectively under mild atmospheric conditions to give the corresponding biaryl compounds in a high yield. The single-crystal X-ray analysis of a Pd(II) complex of 1 revealed its coordination structure, in which two homochiral molecules form a dimer, suggesting that triptycene could provide a chiral environment for asymmetric organic transformations. In fact, optically active 1 obtained by optical resolution showed good enantioselectivity in the palladium-catalyzed asymmetric hydrosilylation of styrene, which represents, for the first time, the asymmetric catalytic activity of triptycene-based monophosphine ligands.
- リンク情報
- ID情報
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- DOI : 10.1021/acsomega.7b00200
- ISSN : 2470-1343
- PubMed ID : 31457552
- PubMed Central 記事ID : PMC6640964