Issue 34, 2018

A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactions

Abstract

A bromo-capped metal–metal bonded diruthenium(I,I) complex Ru2(CO)4(PIN)2Br2 (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with 1 and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating in situ Br2 generation. Complex 2, an iodide analogue of 1, is also synthesized. The reaction of 2 with N-iodosuccinimide releases I2, which is confirmed by the starch-iodine test. The catalytic utility of 1 is examined for the bromination of phenol. Catalyst 1, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst 1 in the presence of NBS, K2CO3 and TsNH2.

Graphical abstract: A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactions

Supplementary files

Article information

Article type
Paper
Submitted
08 5 2018
Accepted
18 6 2018
First published
18 6 2018

Dalton Trans., 2018,47, 11917-11924

A bromo-capped diruthenium(I,I) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactions

G. Sengupta, P. Pandey, S. De, R. Ramapanicker and J. K. Bera, Dalton Trans., 2018, 47, 11917 DOI: 10.1039/C8DT01851K

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