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Investigation on reactivity of non-classical carbenes with sterically hindered Lewis acid, B(C6F5)3 under inert and open conditions

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Abstract

Reactions of B(C6F5)3 with abnormal N-heterocyclic carbene (aNHC), L1 and cyclic (alkyl)(amino) carbene (cAAC), L2 in the presence of moisture as well as in its absence, have been investigated in toluene. Reaction of aNHC with 1 equivalent of B(C6F5)3 under inert condition produced classical Lewis acid-base adduct, [L1.B(C6F5)3], 1. Further, probing the same reaction with cyclic (alkyl)(amino) carbene (cAAC), having different electronic property, led to the isolation of [L2.B(C6F5)3], 2 under inert condition. Interestingly, reaction of aNHC or cAAC with 1 equivalent of B(C6F5)3 in the presence of moisture resulted in water splitting leading to the formation of [L1-H][(OH)B(C6F5)3], 3 and [L2-H][(OH)B(C6F5)3, 4. All these compounds (1-4) were characterized in solution by 1H, 13C, 19F and 11B NMR spectroscopy. Additionally, the solid-state structures were unambiguously established by crystallographic analysis of compounds 1-4.

Reactions of B(C6F5)3 with abnormal N-heterocyclic carbene or cyclic (alkyl)(amino) carbene in absence and in presence of moisture in toluene led to the formation of B(C6F5)3-carbene 1:1 adducts and water splitting products, respectively.

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Acknowledgements

The authors thank Prof. Swadhin Kumar Mandal of Indian Institute of Science Education and Research-Kolkata for his encouragement and helpful scientific discussions. AT and SRB thank the DST, India for financial support. PKV and GVK are thankful to UGC for research fellowship.

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology Rourkela, Rourkela, 769 008, India

    ARUNABHA THAKUR & SUSHIL RANJAN BHATTA

  2. Department of Chemical Science, Indian Institute of Science Education and Research, Kolkata, India

    PAVAN K VARDHANAPU & GONELA VIJAYKUMAR

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  1. ARUNABHA THAKUR
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  2. PAVAN K VARDHANAPU
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Correspondence to ARUNABHA THAKUR.

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Supplementary Information (SI)

Spectroscopic data for compounds 1-4. CCDCs 1052864–1052867 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (+ 44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).

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THAKUR, A., VARDHANAPU, P.K., VIJAYKUMAR, G. et al. Investigation on reactivity of non-classical carbenes with sterically hindered Lewis acid, B(C6F5)3 under inert and open conditions. J Chem Sci 128, 613–620 (2016). https://doi.org/10.1007/s12039-016-1049-5

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  • DOI: https://doi.org/10.1007/s12039-016-1049-5

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