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Title
Japanese: 
English:Synthesis and Catalytic Applications of a Triptycene-Based Monophosphine Ligand for Palladium-Mediated Organic Transformations 
Author
Japanese: Leung King Chi, 石割文崇, 庄子良晃, Tsuyoshi Nishikawa, Ryohei Takeda, Yuuya Nagata, Michinori Suginome, Yasuhiro Uozumi, Yoichi M. A. Yamada, 福島孝典.  
English: Franco King Chi Leung, Fumitaka Ishiwari, Yoshiaki Shoji, Tsuyoshi Nishikawa, Ryohei Takeda, Yuuya Nagata, Michinori Suginome, Yasuhiro Uozumi, Yoichi M. A. Yamada, Takanori Fukushima.  
Language English 
Journal/Book name
Japanese: 
English:ACS Omega 
Volume, Number, Page 2    5    pp. 1930–1937
Published date May 9, 2017 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL http://pubsdc3.acs.org/doi/full/10.1021/acsomega.7b00200
 
DOI https://doi.org/10.1021/acsomega.7b00200
Abstract 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.

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