Issue 8, 2023

Diversity-oriented synthesis of medium-sized cyclophanes via the photo-fries rearrangement of N-aryl lactams

Abstract

Macrocycles containing a cyclophane skeleton have intrigued scientists for many years due to their sophisticated structure and wide use in materials science and molecular recognition processes. Preparing macrocycles with a cyclophane skeleton, however, is inherently difficult due to the high entropic cost of ring-closing. Herein, we report a green and sustainable protocol for the preparation of structurally diverse cyclophane skeletons via a light-promoted intramolecular Fries-type rearrangement, starting from simple N-aryl lactams. This operationally straightforward reaction proceeds with excellent atom economy, solely under light irradiation without any catalysts or additives and provides a practical route to ortho- and para-cyclophanes with never-seen-before architectures.

Graphical abstract: Diversity-oriented synthesis of medium-sized cyclophanes via the photo-fries rearrangement of N-aryl lactams

Supplementary files

Article information

Article type
Paper
Submitted
31 Mar 2023
Accepted
14 Apr 2023
First published
25 Apr 2023

React. Chem. Eng., 2023,8, 1923-1929

Diversity-oriented synthesis of medium-sized cyclophanes via the photo-fries rearrangement of N-aryl lactams

P. Szcześniak and B. Furman, React. Chem. Eng., 2023, 8, 1923 DOI: 10.1039/D3RE00193H

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