Henry, M. C., Senn, H. M. and Sutherland, A. (2019) Synthesis of functionalized indolines and dihydrobenzofurans by iron and copper catalyzed aryl C-N and C-O bond formation. Journal of Organic Chemistry, 84(1), pp. 346-364. (doi: 10.1021/acs.joc.8b02888) (PMID:30520304)
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Abstract
A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N- or O-arylation step leading to indolines, dihydrobenzofurans and six-membered analogues. The general applicability and functional group tolerance of this method was exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Henry, Mr Martyn and Senn, Dr Hans and Sutherland, Professor Andrew |
| Authors: | Henry, M. C., Senn, H. M., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 06 December 2018 |
| Copyright Holders: | Copyright © 2018 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 84(1): 346-364 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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