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Issue 44, 2017
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Catalyst free boron carbon bond cleavage and facile formation of five-membered PNBCC heterocycles

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Abstract

The [3 + 2] cycloaddition reaction of phosphanyl aminoborane [N(2,6-iPr2C6H3)(PPh2)(BCy2)] (1) with activated alkynes led to boron and phosphorus containing five-membered heterocycles [(2,6-iPr2C6H3)NPPh2(CO2R)C–C(Cy)(CO2R)(BCy)] [R = Me (2), Et (3) and H (4)] with facile cleavage of the B–C bond and concomitant formation of a P–C bond with an ylidic character. DFT calculations indicate that 1 can be considered as a non-conjugated 1,3-dipole having two reaction centers viz., a nucleophilic P-center and an electrophilic B-center. The reaction of 1 with the alkynes proceeds through a stepwise dipolar addition mechanism, followed by the migration of the cyclohexyl group from the B-atom to the adjacent C-atom.

Graphical abstract: Catalyst free boron carbon bond cleavage and facile formation of five-membered PNBCC heterocycles

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Publication details

The article was received on 22 Sep 2017, accepted on 09 Oct 2017 and first published on 09 Oct 2017


Article type: Communication
DOI: 10.1039/C7DT03565A
Citation: Dalton Trans., 2017,46, 15190-15194
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    Catalyst free boron carbon bond cleavage and facile formation of five-membered PNBCC heterocycles

    R. Dasgupta, A. Panda, S. Pal, P. Veetil Muhasina, S. De, P. Parameswaran and S. Khan, Dalton Trans., 2017, 46, 15190
    DOI: 10.1039/C7DT03565A

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