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. 2017 Mar 31:13:639-643.
doi: 10.3762/bjoc.13.62. eCollection 2017.

Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst

Abdusalom A Suleymanov  1 , Dmitry V Vasilyev  1 , Valentin V Novikov  1 , Yulia V Nelyubina  1 , Dmitry S Perekalin  1
Affiliations

Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst

Abdusalom A Suleymanov et al. Beilstein J Org Chem. .

Abstract

1,11-Dien-6-ynes undergo cycloisomerization in the presence of the cobalt catalytic system CoBr2/phosphine ligand/Zn/ZnI2 giving cyclohexene, diene or cyclopropane structures depending on the type of the phosphine ligand. This unpredictable behaviour suggests that, although the availability of the cobalt catalytic system is appealing, the development of well-defined catalysts is desirable for further progress.

Keywords: catalysis; cobalt; cyclization; enynes; ligands.

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Figures

Scheme 1
Scheme 1
Examples of metal-catalyzed transformations of 1,11-dien-6-ynes.
Scheme 2
Scheme 2
Cobalt-catalyzed cycloisomerizations of 1,11-dien-6-ynes.
Scheme 3
Scheme 3
Possible mechanism for formation of the compounds 2–5.
Scheme 4
Scheme 4
Cycloisomerization of the substituted dienyne 1c.
Figure 1
Figure 1
The substituted 1,11-dien-6-ynes that did not undergo cycloisomerization in the presence of the cobalt catalytic system.
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