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Catalyst Free Boron Carbon Bond Cleavage and Facile Formation of Five-membered PNBCC Heterocycles

Abstract

The [3+2] cycloaddition reaction of phosphanyl aminoborane [N(2,6-iPr2C6H3)(PPh2)(BCy2)] (1) with activated alkynes led to the boron, 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 B-C bond and concomitant formation of a P–C bond with an ylidic character. DFT calculations indicate that 1 can be considered as 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 cyclohexyl group from the B-atom to the adjacent C-atom.

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Publication details

The article was accepted on 09 Oct 2017 and first published on 09 Oct 2017


Article type: Communication
DOI: 10.1039/C7DT03565A
Citation: Dalton Trans., 2017, Accepted Manuscript
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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, Accepted Manuscript , DOI: 10.1039/C7DT03565A

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