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Phenyl vs. ferrocenyl cyclometallation selectivity: diastereoselective synthesis of an enantiopure iridacycle

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.
1434-1948
1-5
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.
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, 1-5. (doi:10.1002/ejic.201600904).

Record type: Article

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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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
ORCID for Peter Horton: ORCID iD orcid.org/0000-0001-8886-2016
ORCID for Simon Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 13 Sep 2016 09:40
Last modified: 17 Dec 2019 06:39

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Contributors

Author: Ross A. Arthurs
Author: Peter Horton ORCID iD
Author: Simon Coles ORCID iD
Author: Christopher J. Richards

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