Synlett 2017; 28(17): 2205-2211
DOI: 10.1055/s-0036-1589081
synpacts
© Georg Thieme Verlag Stuttgart · New York

Highly Strained para-Phenylene-Bridged Macrocycles from Unstrained 1,4-Diketo Macrocycles

Nirmal K. Mitra, Caroline P. Merryman, Bradley L. Merner*
  • Department of Chemistry and Biochemistry, Auburn University, Auburn, AL, 36849, USA   Email: blm0022@auburn.edu
Further Information

Publication History

Received: 31 May 2017

Accepted after revision: 23 June 2017

Publication Date:
22 August 2017 (eFirst)

Abstract

The conversion of macrocyclic 1,4-diketones to highly strained para-phenylene rings has recently been reported by our laboratory. This synthetic strategy represents a non-cross-coupling-based approach to arene-bridged macrocycles, and an alternative to palladium- and nickel-mediated processes. In this Synpacts article we discuss the development of endgame aromatization protocols for the synthesis of increasingly strained arene systems, as well as potential advantages of the macrocyclic 1,4-diketone approach to selectively functionalized benzenoid macrocycles for future complexity building reactions.

1 Introduction

2 A Non-Cross-Coupling-Based Approach to Arene-Bridged Macro cycles

3 Macrocyclic 1,4-Diketones: Streamlined Synthesis and Size-­Dependent Diastereoselective Grignard Reactions

4 Dehydrative Aromatization Reactions: A Powerful Tool for Synthesizing Highly Strained para-Phenylene Units

5 Conclusion