Issue 8, 2019

Ir-Catalyzed ring-opening of oxa(aza)benzonorbornadienes with water or alcohols

Abstract

A highly efficient Ir-catalyzed ring-opening reaction of oxa(aza)benzonorbornadienes with water was firstly developed, which afforded a mild access to substituted dihydronaphthalene products with excellent yields (up to 99%) within 30 min. Further studies showed that when we used proton containing nucleophiles such as alcohols, we obtained the corresponding trans-1,2-disubstituted dihydronaphthalenol products in excellent yields (up to 99%) within 30 min. In addition, these two reactions not only occurred with low catalyst loading (1 mol% for most substrates), but also led to the desired products in excellent yields in the absence of a bisphosphine ligand. Another interesting finding was that 1-naphthylamine 6 was synthesized through the aromatization reaction of ring-opening product 3f using Lewis acid BF3·OEt2 as a catalyst.

Graphical abstract: Ir-Catalyzed ring-opening of oxa(aza)benzonorbornadienes with water or alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
25 Dec 2018
Accepted
20 Feb 2019
First published
06 Mar 2019

Org. Chem. Front., 2019,6, 1151-1156

Ir-Catalyzed ring-opening of oxa(aza)benzonorbornadienes with water or alcohols

X. Yang, W. Yang, Y. Yao, Y. Deng and D. Yang, Org. Chem. Front., 2019, 6, 1151 DOI: 10.1039/C8QO01403E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements