Issue 50, 2020

Storage and release of two electrons from an electron-rich carbon–carbon bond: boron mediated reversible coupling of DMAP and 9-azajulolidine

Abstract

This manuscript describes the preparation of [{(dpp-bian)BBr}Li(DME)3] (2, dpp-bian = 1,2-bis[(2,6-diisopropylphenyl) imino]acenaphthene) and [{(dpp-bian)BL}+Br] (5, L = DMAP; 6, L = 9-azajulolidine). The 4,4-coupling of DMAP and 2,2-coupling of 9-azajulolidine can be achieved either by the reaction of 2 with L, or by one-electron reduction of borenium cations 5 and 6. Oxidation of 3 and 4 leads to C–C cleavage and regeneration of 5 and 6. All new compounds have been structurally characterized.

Graphical abstract: Storage and release of two electrons from an electron-rich carbon–carbon bond: boron mediated reversible coupling of DMAP and 9-azajulolidine

Supplementary files

Article information

Article type
Communication
Submitted
28 Feb 2020
Accepted
12 May 2020
First published
12 May 2020

Chem. Commun., 2020,56, 6794-6797

Storage and release of two electrons from an electron-rich carbon–carbon bond: boron mediated reversible coupling of DMAP and 9-azajulolidine

Y. Cui, L. Xiang, J. Wang, C. Li, W. Hao and Q. Ye, Chem. Commun., 2020, 56, 6794 DOI: 10.1039/D0CC01575J

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