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. 2018 Aug 14;47(32):10853-10856.
doi: 10.1039/c8dt02435a.

Formation of borata-alkene/iminium zwitterions by ynamine hydroboration

Long Wang  1 , Zhongbao Jian, Constantin G Daniliuc, Gerald Kehr, Gerhard Erker
Affiliations

Formation of borata-alkene/iminium zwitterions by ynamine hydroboration

Long Wang et al. Dalton Trans. .

Abstract

The ynamine TMP-C[triple bond, length as m-dash]C-CH3 adds HB(C6F5)2 to give the unsaturated C2-bridged N/B FLP 5. Compound 5 shows the structural data indicating a marked participation of the zwitterionic mesomeric borata-alkene/iminium form. It splits dihydrogen at r.t. with Z- to E-isomerization at the central C[double bond, length as m-dash]C double bond. Hydroboration of the ynamine Me3Si-C[triple bond, length as m-dash]C-NiPr2 with HB(C6F5)2 yields a N/B FLP that shows a strongly distorted central C[double bond, length as m-dash]C double bond with a rotation of the planes of the substituent pairs at its ends by ca. 57°.

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