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Issue 30, 2020
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Gold-catalyzed dual C–C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature

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Abstract

We report a catalytic skeletal rearrangement of biphenylenes with a pendant alkyne moiety at room temperature by a cationic gold catalyst, which involves the cleavage of two bonds: the C–C bond of biphenylene and the C(sp)–C(sp2 or sp3) bond. Experimental and theoretical studies revealed that the reaction mechanism included π-activation of the alkyne, ring expansion and 1,2-carbon shift.

Graphical abstract: Gold-catalyzed dual C–C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature

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Supplementary files

Article information


Submitted
12 Jun 2020
Accepted
09 Jul 2020
First published
09 Jul 2020

Org. Biomol. Chem., 2020,18, 5826-5831
Article type
Communication

Gold-catalyzed dual C–C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature

H. Takano, S. Okazaki, S. Nishibe, T. Ito, N. Shiozawa, N. Sugimura, K. S. Kanyiva and T. Shibata, Org. Biomol. Chem., 2020, 18, 5826
DOI: 10.1039/D0OB01211D

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