Synthesis of fluorinated fused benzofurans and benzothiophenes: Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides

Ponce Gonzalez, J, Edgar, M, Elsegood, MRJ and Weaver, GW (2011) Synthesis of fluorinated fused benzofurans and benzothiophenes: Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides Org. Biomol. Chem., 9. 2294-2305 - 2294-2305.

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Abstract

Lithium-bromine exchange in 2-bromophenyl perfluoroaryl ethers or sulfides affords fused fluorinated benzofurans or benzothiophenes respectively by SNAr substitution of the adjacent fluorine in the perfluoroaryl substituent. The structures of the new compounds were confirmed by NMR spectroscopy and single crystal X-ray diffraction analysis. In the case of 2-bromophenyl tetrafluoropyrid-4-yl ether, lithiation promoted a Smiles-type rearrangement which led to formation of 4-(2-hydroxyphenyl)tetrafluoropyridine, for which the structure was confirmed by X-ray crystallography.

Item Type:	Article
Divisions :	Surrey research (other units)
Authors :	Ponce Gonzalez, J, Edgar, M, Elsegood, MRJ and Weaver, GW
Date :	2011
DOI :	10.1039/C0OB00790K
Related URLs :	Publisher
Depositing User :	Symplectic Elements
Date Deposited :	17 May 2017 13:33
Last Modified :	25 Jan 2020 00:07
URI:	http://epubs.surrey.ac.uk/id/eprint/839659

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