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

Hideaki Takano; Sari Okazaki; Shun Nishibe; Takeharu Ito; Natsumi Shiozawa; Natsuhiko Sugimura; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1039/d0ob01211d

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

Hideaki Takano, Sari Okazaki, Shun Nishibe, Takeharu Ito, Natsumi Shiozawa, Natsuhiko Sugimura, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5826-5831
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	30
DOIs	https://doi.org/10.1039/d0ob01211d
Publication status	Published - 2020 Aug 14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d0ob01211d

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title = "Gold-catalyzed dual C-C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature",

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.",

author = "Hideaki Takano and Sari Okazaki and Shun Nishibe and Takeharu Ito and Natsumi Shiozawa and Natsuhiko Sugimura and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: This work was supported by the Waseda University Grant for Special Research Projects (New Developments in Research, 2019N-020). H. T. is grateful to the Japan Society for the Promotion of Science for financial support (JSPS KAKENHI Grant Number 18J13634). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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doi = "10.1039/d0ob01211d",

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T1 - Gold-catalyzed dual C-C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature

AU - Takano, Hideaki

AU - Okazaki, Sari

AU - Nishibe, Shun

AU - Ito, Takeharu

AU - Shiozawa, Natsumi

AU - Sugimura, Natsuhiko

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by the Waseda University Grant for Special Research Projects (New Developments in Research, 2019N-020). H. T. is grateful to the Japan Society for the Promotion of Science for financial support (JSPS KAKENHI Grant Number 18J13634). Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/8/14

Y1 - 2020/8/14

N2 - 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.

AB - 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.

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U2 - 10.1039/d0ob01211d

DO - 10.1039/d0ob01211d

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SN - 1477-0520

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EP - 5831

JO - Organic and Biomolecular Chemistry

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IS - 30

ER -

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

Abstract

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