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Synfacts 2023; 19(10): 0987
DOI: 10.1055/s-0042-1752206
Metals in Synthesis

Silver(I)-Catalyzed Rearrangement of 1,4-Disubstituted Cubanes to 1,3- or 2,6-Disubstituted Cuneanes

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
Smith E, Jones KD, O’Brien L, Argent SP, Salome C, Lefebvre Q, Valery A, Böcü M, Newton GN, Lam HW. * University of Nottingham, UK
Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.

J. Am. Chem. Soc. 2023;
145: 16365-16373
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Key words

cubanes - cuneanes - rearrangement - silver catalysis

Significance

Lam and co-workers disclosed a silver(I)-catalyzed rearrangement of 1,4-disubstituted cubanes to 1,3- or 2,6-disubstituted cuneanes. The regioselectivity is strongly dependent on the electronic character of the substituents.


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Comment

To explore those strained hydrocarbons as isosteres of 1,3-disubstituted benzenes, an analogue of the anticancer drug sonidegib was prepared by replacing the 1,2,3-trisubstituted benzene with a 1,3-disubstituted cuneane.


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Publication History

Article published online:
14 September 2023

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