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Issue 6, 2018
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Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

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Abstract

The trifunctional P/B/B frustrated Lewis pairs 11a–c featuring bulky aryl groups at phosphorus [Dmesp (a), Tipp (b), Mes* (c)] react with H2 by heterolytic hydrogen splitting followed by cleavage of HB(C6F5)2 to give the zwitterionic six-membered heterocyclic PH phosphonium/borate products 14a–c. Compounds 11a,b react with carbon monoxide by means of a Lewis acid induced CO insertion/rearrangement sequence that eventually results in the formation of the macrocyclic dimers 17a,b. The respective carbonylation reaction of the Mes*P/B/B FLP gives the macrocyclic trimer 18c. The new products were characterized spectroscopically and by X-ray diffraction and the reaction mechanism was analyzed by DFT calculations.

Graphical abstract: Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

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Publication details

The article was received on 10 Oct 2017, accepted on 13 Dec 2017 and first published on 14 Dec 2017


Article type: Edge Article
DOI: 10.1039/C7SC04394E
Citation: Chem. Sci., 2018,9, 1544-1550
  • Open access: Creative Commons BY license
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    Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

    L. Wang, S. Dong, C. G. Daniliuc, L. Liu, S. Grimme, R. Knitsch, H. Eckert, M. R. Hansen, G. Kehr and G. Erker, Chem. Sci., 2018, 9, 1544
    DOI: 10.1039/C7SC04394E

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