Synthesis 2019; 51(13): 2632-2647
DOI: 10.1055/s-0037-1610714
short review
© Georg Thieme Verlag Stuttgart · New York

Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates

Further Information

Publication History

Received: 28 February 2019

Accepted after revision: 18 April 2019

Publication Date:
21 May 2019 (online)


Abstract

Micellar reaction conditions, in a predominantly aqueous medium, have been developed for transformations commonly used by synthetic chemists working in the pharmaceutical industry to discover and develop drug candidates. The reactions covered in this review are the Suzuki–Miyaura, Miyaura borylation, Sonogashira coupling, transition-metal-catalysed CAr–N coupling, SNAr, amidation, and nitro reduction. Pharmaceutically relevant examples of these applications will be used to show how micellar conditions can offer advantages in yield, operational ease, amount of waste generated, transition-metal catalyst loading, and safety over the use of organic solvents, irrespective of the setting in which they are used.

1 Introduction

2 Micelles as Solubilising Agents

3 Micelles as Nanoreactors

4 Designer Surfactants

5 A Critical Evaluation of the Case for Chemistry in Micelles

6 Scope of Review

7 Suzuki–Miyaura Coupling

8 Miyaura Borylation

9 Sonogashira Coupling

10 Transition-Metal-Catalysed CAr–N Couplings

11 SNAr

12 Amidation

13 Nitro Reduction

14 Micellar Sequences

15 Summary and Outlook

 
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