Imperial College London
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Dr James A Bull

Faculty of Natural Sciences, Department of Chemistry

Reader in Synthetic Chemistry
 
 
 
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Contact

 

+44 (0)20 7594 5811j.bull Website

 
 
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Location

 

501bMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Croft:2019:10.1002/ejoc.201900498,
author = {Croft, RA and Dubois, MAJ and Boddy, AJ and Denis, C and Lazaridou, A and Voisin-Chiret, AS and Bureau, R and Choi, C and Mousseau, JJ and Bull, JA},
doi = {10.1002/ejoc.201900498},
journal = {European Journal of Organic Chemistry},
pages = {5385--5395},
title = {Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp<sup>3</sup>-sp<sup>2</sup> Coupling of Medicinally Relevant Fragments},
url = {http://dx.doi.org/10.1002/ejoc.201900498},
volume = {2019},
year = {2019}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.
AU  - Croft,RA
AU  - Dubois,MAJ
AU  - Boddy,AJ
AU  - Denis,C
AU  - Lazaridou,A
AU  - Voisin-Chiret,AS
AU  - Bureau,R
AU  - Choi,C
AU  - Mousseau,JJ
AU  - Bull,JA
DO  - 10.1002/ejoc.201900498
EP  - 5395
PY  - 2019///
SN  - 1434-193X
SP  - 5385
TI  - Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp<sup>3</sup>-sp<sup>2</sup> Coupling of Medicinally Relevant Fragments
T2  - European Journal of Organic Chemistry
UR  - http://dx.doi.org/10.1002/ejoc.201900498
UR  - http://hdl.handle.net/10044/1/70546
VL  - 2019
ER  -
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