Issue 98, 2017

Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner

Abstract

We report a transition metal-free dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene (1) under mild conditions, in which trimethylsilyl halide and 4,4′-bipyridine were generated as byproducts. The synthetic protocol for this dehalogenation reaction was effective for a wide scope of dibromo compounds as substrates while keeping the various functional groups intact. Furthermore, the reduction of vicinal dichloro alkanes and vicinal dibromo alkenes also proceeded in a salt-free manner to afford the corresponding alkenes and alkynes.

Graphical abstract: Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner

Supplementary files

Article information

Article type
Communication
Submitted
21 Sep 2017
Accepted
20 Nov 2017
First published
20 Nov 2017

Chem. Commun., 2017,53, 13157-13160

Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner

S. Rej, S. Pramanik, H. Tsurugi and K. Mashima, Chem. Commun., 2017, 53, 13157 DOI: 10.1039/C7CC07377A

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