4, 4′‐ and 5, 5′‐Functionalized (S)‐ and (R)‐2, 2′‐Bis(diphenylphosphanyl)‐1, 1′‐binaphthyl Oxide Derivatives12. Issue 14 (16th July 2013)

• Record Type: Journal Article
• Authors: Wahyu Lestari, Witri; Zaake‐Hertling, Haldor; Lönnecke, Peter; Hey‐Hawkins, Evamarie
• Is Part Of: Zeitschrift für anorganische und allgemeine Chemie. Volume 639:Issue 14(2013)
• Page Start: 2589
• Page End: 2596
• Publication Date: 2013-07-16
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/zaac.201300278
• Languages: English
• ISSNs: 0044-2313

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A series of 4, 4′‐ and 5, 5′‐functionalized (<italic>S</italic>)‐ and (<italic>R</italic>)‐2, 2′‐bis(diphenylphosphanyl)‐1, 1′‐binaphthyl oxide (BINAPO) derivatives were prepared by Suzuki‐Miyaura coupling from 4, 4′‐ and 5, 5′‐dibromo‐BINAPO and the corresponding boronic acid, <italic>R</italic>B(OH)₂ [<italic>R</italic> = 4‐(methoxycarbonyl)phenyl, 3‐pyridyl and 4‐pyridyl]. The carboxylic acid‐substituted BINAPO derivatives were obtained from the esters by saponification with NaOH. The novel BINAPO derivatives were fully characterized by NMR (¹H, ¹³C, ³¹P), IR spectroscopy, and mass spectrometry, and for (<italic>S</italic>)‐4, 4′‐bis(3‐pyridyl)‐BINAPO, (<italic>S</italic>)‐5, 5′‐bis(3‐pyridyl)‐BINAPO, and (<italic>S</italic>)‐ and (<italic>R</italic>)‐4, 4′‐bis(4‐carboxyphenyl)‐BINAPO also by X‐ray crystallography. They are thermally stable up to 400–440 °C as determined by DTA/TG analysis.</p> </abstract>