Synthesis of functionalized indolines and dihydrobenzofurans by iron and copper catalyzed aryl C-N and C-O bond formation

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 Sutherland, Dr Andrew and Senn, Dr Hans
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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
701101EPSRC 2015 DTPMary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M508056/1R&I - RESEARCH STRATEGY & INNOVATION