Expedient access to C-aryl linked saturated heterocyclic motifs

  • Peter Sharp Campbell

Student thesis: Doctoral Thesis

Abstract

Over the past decade, there has been a significant increase in the overall degree of saturation in candidate molecules. Increased sp3 character has been linked to a variety of improved physicochemical properties, including greater solubility and an improved likelihood of clinical success. Based on this, a range of methods have been developed to synthesise compounds with high saturation, particularly with respect to sp2-sp3 cross-coupling reactions. Many of these approaches suffer from severe drawbacks, such as a lack of generality and the requirement for bespoke, complex catalyst systems. After initial investigation into a Suzuki-Miyaura approach towards the molecules of interest, the development of a one-pot Suzuki-Miyaura-hydrogenation was explored. This method was found to be highly general and tolerant of a wide range of functionalities. Scheme 1: Developed Suzuki-Miyaura-hydrogenation methodology [Figure available in print copy]. Subsequently, the methodology was extended to allow for a transfer hydrogenation protocol. This process was broadly applicable to a range of synthetic methods, including an array format and the synthesis of multiple biologically active compounds. Scheme 2: Developed Suzuki-Miyaura-transfer-hydrogenation methodology [Figure available in print copy].
Date of Award1 Jan 2018
LanguageEnglish
Awarding Institution
  • University Of Strathclyde
SponsorsUniversity of Strathclyde & EPSRC (Engineering and Physical Sciences Research Council)
SupervisorCraig Jamieson (Supervisor) & (Supervisor)

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