Phenyl vs. ferrocenyl cyclometallation selectivity: diastereoselective synthesis of an enantiopure iridacycle
Phenyl vs. ferrocenyl cyclometallation selectivity: diastereoselective synthesis of an enantiopure iridacycle
Ferrocenyl (Fc) and phenyl (Ph) containing imines FcCH=NCH(R)Ph and FcCH(R)N=CHPh (R = H and Me) were cycloiridated using [Cp*IrCl2]2 with NaOAc in CH2Cl2. All resulted in the formation of neutral chloride ligated half-sandwich iridacycles as a result of ortho-phenyl and not alpha-ferrocenyl C–H activation. The complexes derived from FcCH=NCH(R)Ph (R = H,Me) were obtained as a mixture of E and Z imine isomers, and with R = Me the product obtained from the (S)-imine was isolated by recrystallisation as a single diastereoisomer. The configuration was determined by an X-ray crystal structure analysis as SC,RIr,E.
1-5
Arthurs, Ross A.
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Horton, Peter
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Coles, Simon
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Richards, Christopher J.
bf1ec9f1-3545-450b-b64c-2984e311dfb6
Arthurs, Ross A.
d88e1b07-6886-422f-810c-aa293043854d
Horton, Peter
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Richards, Christopher J.
bf1ec9f1-3545-450b-b64c-2984e311dfb6
Arthurs, Ross A., Horton, Peter, Coles, Simon and Richards, Christopher J.
(2016)
Phenyl vs. ferrocenyl cyclometallation selectivity: diastereoselective synthesis of an enantiopure iridacycle.
European Journal of Inorganic Chemistry, .
(doi:10.1002/ejic.201600904).
Abstract
Ferrocenyl (Fc) and phenyl (Ph) containing imines FcCH=NCH(R)Ph and FcCH(R)N=CHPh (R = H and Me) were cycloiridated using [Cp*IrCl2]2 with NaOAc in CH2Cl2. All resulted in the formation of neutral chloride ligated half-sandwich iridacycles as a result of ortho-phenyl and not alpha-ferrocenyl C–H activation. The complexes derived from FcCH=NCH(R)Ph (R = H,Me) were obtained as a mixture of E and Z imine isomers, and with R = Me the product obtained from the (S)-imine was isolated by recrystallisation as a single diastereoisomer. The configuration was determined by an X-ray crystal structure analysis as SC,RIr,E.
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10.1002ejic.201600904_Final Author Manuscript.pdf
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Accepted/In Press date: 22 July 2016
e-pub ahead of print date: 30 August 2016
Organisations:
Characterisation and Analytics
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Local EPrints ID: 400214
URI: http://eprints.soton.ac.uk/id/eprint/400214
ISSN: 1434-1948
PURE UUID: a3f64626-aaa8-4536-95a1-6ab74d794d53
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Date deposited: 13 Sep 2016 09:40
Last modified: 15 Mar 2024 05:53
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Author:
Ross A. Arthurs
Author:
Peter Horton
Author:
Christopher J. Richards
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