Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles

Chemistry

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Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles. / Cooper, Lisa; Alonso, José Miguel; Eagling, Louise et al.
In: Chemistry - A European Journal, Vol. 24, No. 23, 02.02.2018, p. 6105-6114.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Cooper, L, Alonso, JM, Eagling, L, Newson, H, Herath, S, Thomson, C, Lister, A, Howsham, C, Cox, B & Paz Muñoz, M 2018, 'Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles', Chemistry - A European Journal, vol. 24, no. 23, pp. 6105-6114. https://doi.org/10.1002/chem.201705417

APA

Cooper, L., Alonso, J. M., Eagling, L., Newson, H., Herath, S., Thomson, C., Lister, A., Howsham, C., Cox, B., & Paz Muñoz, M. (2018). Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles. Chemistry - A European Journal, 24(23), 6105-6114. https://doi.org/10.1002/chem.201705417

Vancouver

Cooper L, Alonso JM, Eagling L, Newson H, Herath S, Thomson C et al. Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles. Chemistry - A European Journal. 2018 Feb 2;24(23):6105-6114. doi: 10.1002/chem.201705417

Author

Cooper, Lisa ; Alonso, José Miguel ; Eagling, Louise et al. / Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles. In: Chemistry - A European Journal. 2018 ; Vol. 24, No. 23. pp. 6105-6114.

Bibtex

@article{5a319ca827774950aaec9049e88598d5,

title = "Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles",

abstract = "Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3'-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3'-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.",

keywords = "platinum, allene, indole, bisindolylmethane, mechanism",

author = "Lisa Cooper and Alonso, {Jos{\'e} Miguel} and Louise Eagling and Helen Newson and Sachini Herath and Christopher Thomson and Andrew Lister and Catherine Howsham and Brian Cox and {Paz Mu{\~n}oz}, Mar{\'i}a",

year = "2018",

month = feb,

day = "2",

doi = "10.1002/chem.201705417",

language = "English",

volume = "24",

pages = "6105--6114",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "23",

}

RIS

TY - JOUR

T1 - Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles

AU - Cooper, Lisa

AU - Alonso, José Miguel

AU - Eagling, Louise

AU - Newson, Helen

AU - Herath, Sachini

AU - Thomson, Christopher

AU - Lister, Andrew

AU - Howsham, Catherine

AU - Cox, Brian

AU - Paz Muñoz, María

PY - 2018/2/2

Y1 - 2018/2/2

N2 - Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3'-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3'-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

AB - Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3'-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3'-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

KW - platinum

KW - allene

KW - indole

KW - bisindolylmethane

KW - mechanism

U2 - 10.1002/chem.201705417

DO - 10.1002/chem.201705417

M3 - Journal article

VL - 24

SP - 6105

EP - 6114

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 23

ER -

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