Ring Closing Metathesis Approach for the Synthesis of o‐Terphenyl Derivatives

Abstract

A linear synthesis of o‐terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl‐1,2‐diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization‐driven dehydration then leads to a diverse set of electron rich and electron deficient o‐terphenyls. Furthermore, oxidative coupling of electron rich o‐terphenyls provides the corresponding triphenylene derivatives.

Ready Access to Densely Substituted Furans Using Tsuji–Wacker-Type Cyclization

“…The required starting materials were prepared from different amino acids by using a known protocol . A variety of ketones 6 were subjected to allyl Grignard and indium metal-mediated Barbier type reaction to have alkenyl diols 7a–d and 8a–g (Scheme ). On the other hand, different benzoins 9 were prepared through known protocols .…”

Application of Olefin Metathesis in the Synthesis of Carbo- and Heteroaromatic Compounds—Recent Advances

“…The proposed synthetic pathway involves RCM for the synthesis of a tricyclic skeleton and subsequent aromatization step. It enables the synthesis of symmetrical and unsymmetrical o -terphenyls containing both electron-rich and electron-deficient groups ( Scheme 43 ) [ 57 ].…”

Molecular dynamics and kinetics of isothermal cold crystallization with tunable dimensionality in a molecular glass former, 5′-(2,3-difluorophenyl)-2′-ethoxy-4-pentyloxy-2,3-difluorotolane

“…45–51 OTP is broadly applied as a raw material for organic synthesis and pharmaceutical intermediate, and its derivatives are used in organic light-emitting diodes (OLEDs). 52–54 The chemically more complex molecule of DFP25DFT possesses polar groups and alkyl chains in alkoxy moieties that generally act as a trigger of crystallization. 25,39,55,56…”

“…[45][46][47][48][49][50][51] OTP is broadly applied as a raw material for organic synthesis and pharmaceutical intermediate, and its derivatives are used in organic light-emitting diodes (OLEDs). [52][53][54] The chemically more complex molecule of DFP25DFT possesses polar groups and alkyl chains in alkoxy moieties that generally act as a trigger of crystallization. 25,39,55,56 Fluorination of the molecule increases the dynamic viscosity and density of the material and the intermolecular interactions, fostering crystal formation.…”