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Reactions of Grignard Reagents with Tin-Corrole Complexes: Demetalation Strategy and σ-Methyl/Phenyl Complexes

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School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar − 751005, India
*E-mail: [email protected] (S.K.).
Cite this: Organometallics 2014, 33, 22, 6550–6556
Publication Date (Web):October 20, 2014
https://doi.org/10.1021/om500861p
Copyright © 2014 American Chemical Society

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    Abstract

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    An efficient, mild, and one-step methodology for the conversion of tin-corroles to the corresponding free base corroles has been developed. The Grignard reagent, namely, methylmagnesium chloride, is responsible for the facile demetalation of tin-corroles. In an optimized reaction, almost complete destannation is observed using methylmagnesium chloride in a representative corrolato-Sn(IV)-chloride complex. This particular protocol has also been proven to be versatile on a wide variety of corrolato-Sn(IV)-chloride substrates. Similar Grignard reagents, namely, methyl/phenylmagnesium bromides, however, failed to perform the desired demetalation reaction and rather resulted in the usual σ-methyl/phenyl complexes in good yields. In addition to two novel σ-phenyl complexes and three novel σ-methyl complexes, one new A3-corrole and one new corrolato Sn(IV)chloride have also been synthesized. All the complexes have been thoroughly characterized by various spectroscopic techniques, including single-crystal X-ray structural analysis of the representative complexes. In the single-crystal X-ray data analyses, it was observed that the Sn–N and Sn–C bond distances are shorter than those in the similar tin porphyrin analogues. The 1H NMR spectrum of a representative σ-methyl complex exhibits peaks corresponding to σ-bonded methyl groups in the high field regions at −3.39 ppm.

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    1H NMR spectra of 4A, 4B, 1C, 2C, 1D, 2D, and 4D; ESI-MS spectra of 4A, 4B, 1C, 1D, 2D, and 4D; and packing diagrams of 1C and 2D. This material is available free of charge via the Internet at http://pubs.acs.org. CCDC 1020850–1020851 contain the supplementary crystallographic data for 1C and 2D, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.

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    Cited By

    This article is cited by 11 publications.

    1. Joana F. B. Barata, M. Graça P. M. S. Neves, M. Amparo F. Faustino, Augusto C. Tomé, and José A. S. Cavaleiro . Strategies for Corrole Functionalization. Chemical Reviews 2017, 117 (4) , 3192-3253. https://doi.org/10.1021/acs.chemrev.6b00476
    2. Ritika Kubba, Omprakash Yadav, Pinky Yadav, Natalia Fridman, Anil Kumar. Penta -hexa coordination behaviour of ABA-P(V) corrole. Journal of Molecular Structure 2021, 1243 , 130857. https://doi.org/10.1016/j.molstruc.2021.130857
    3. Woohyun Lee, Xuan Zhan, Jaymee Palma, Jenya Vestfrid, Zeev Gross, David G. Churchill. Minding our P-block and Q-bands: paving inroads into main group corrole research to help instil broader potential. Chemical Communications 2021, 57 (38) , 4605-4641. https://doi.org/10.1039/D1CC00105A
    4. Bratati Patra, Sruti Mondal, Sanjib Kar. Corroles. 2020, 1-24. https://doi.org/10.1002/9781119951438.eibc2729
    5. Sruti Mondal, Pratyush Kumar Naik, Jogesh Kumar Adha, Sanjib Kar. Synthesis, characterization, and reactivities of high valent metal–corrole (M = Cr, Mn, and Fe) complexes. Coordination Chemistry Reviews 2019, 400 , 213043. https://doi.org/10.1016/j.ccr.2019.213043
    6. An-Na Xie, Zhao Zhang, Hua-Hua Wang, Atif Ali, Dong-Xu Zhang, Hui Wang, Liang-Nian Ji, Hai-Yang Liu. DNA-binding, photocleavage and anti-cancer activity of tin(IV) corrole. Journal of Porphyrins and Phthalocyanines 2018, 22 (09n10) , 739-750. https://doi.org/10.1142/S1088424618500256
    7. Bratati Patra, Sajal Kumar Patra, Payel Mukherjee, Yogesh Kumar Maurya, Woormileela Sinha, Sanjib Kar. Grignard Reagent Mediated Demetallation of Silver Corrole Complexes. European Journal of Inorganic Chemistry 2017, 2017 (17) , 2363-2368. https://doi.org/10.1002/ejic.201601549
    8. Woormileela Sinha, Michael G. Sommer, Lara Hettmanczyk, Bratati Patra, Vasileios Filippou, Biprajit Sarkar, Sanjib Kar. Ruthenium–Ruthenium‐Bonded [Bis{corrolato‐ruthenium(III)}] n ( n =0, +1, −1) Complexes: Model Compounds for the Photosynthetic Special Pair. Chemistry – A European Journal 2017, 23 (10) , 2396-2404. https://doi.org/10.1002/chem.201604901
    9. Tamal Chatterjee, Way-Zen Lee, Mangalampalli Ravikanth. Stabilization of hexa-coordinated P( v ) corroles by axial silyloxy groups. Dalton Transactions 2016, 45 (18) , 7815-7822. https://doi.org/10.1039/C6DT00842A
    10. Woormileela Sinha, Luca Ravotto, Paola Ceroni, Sanjib Kar. NIR-emissive iridium( iii ) corrole complexes as efficient singlet oxygen sensitizers. Dalton Transactions 2015, 44 (40) , 17767-17773. https://doi.org/10.1039/C5DT03041B
    11. Antara Garai, Samir Kumar, Woormileela Sinha, Chandra Shekhar Purohit, Ritwick Das, Sanjib Kar. A comparative study of optical nonlinearities of trans-A 2 B-corroles in solution and in aggregated state. RSC Advances 2015, 5 (36) , 28643-28651. https://doi.org/10.1039/C5RA03568F

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