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Synfacts 2015; 11(1): 0076
DOI: 10.1055/s-0034-1379653
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Intramolecular Cyclization of Dihaloalkanes

Contributor(s):
Paul Knochel
,
Thomas Klatt
Xue W, Xu H, Liang Z, Qian Q, * Gong H. * Shanghai University and Zhengzhou University, P. R. of China
Nickel-Catalyzed Reductive Cyclization of Alkyl Dihalides.

Org. Lett. 2014;
16: 4984-4987
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

nickel - cyclization - zinc

Significance

The authors have developed an intramolecular cyclization of nitrogen- and carbon-tethered dihaloalkanes. The protocol is especially effective for five-membered rings and only moderately for six-membered rings. The reactions were performed under mild reactions conditions.


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Comment

The coupling involving secondary alkyl halides appears to be more efficient than the cyclization of primary/primary alkyl dihalides. Interestingly, the construction of a seven-membered ring is less efficient. Side-reactions are intermolecular oligomerization and hydrodehalogenation of the substrate.


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