Ruthenium‐Catalyzed Cycloisomerization of 2,2′‐Diethynyl‐ biphenyls Involving Cleavage of a Carbon–Carbon Triple Bond | Zendy

Matsuda Takanori | Zendy; Kato Kotaro | Zendy; Goya Tsuyoshi | Zendy; Shimada Shingo | Zendy; Murakami Masahiro | Zendy

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Ruthenium‐Catalyzed Cycloisomerization of 2,2′‐Diethynyl‐ biphenyls Involving Cleavage of a Carbon–Carbon Triple Bond

Author(s) -

Matsuda Takanori,

Kato Kotaro,

Goya Tsuyoshi,

Shimada Shingo,

Murakami Masahiro

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201504937

Subject(s) - cycloisomerization , cyclobutene , triple bond , chemistry , ruthenium , moiety , cycloaddition , bond cleavage , catalysis , carbon fibers , reinforced carbon–carbon , ring (chemistry) , phenanthrenes , stereochemistry , medicinal chemistry , double bond , photochemistry , organic chemistry , phenanthrene , materials science , composite number , composite material

A ruthenium complex catalyzes a new cycloisomerization reaction of 2,2′‐diethynylbiphenyls to form 9‐ethynylphenanthrenes, thereby cleaving the carbon–carbon triple bond of the original ethynyl group. A metal–vinylidene complex is generated from one of the two ethynyl groups, and its carbon–carbon double bond undergoes a [2+2] cycloaddition with the other ethynyl group to form a cyclobutene. The phenanthrene skeleton is constructed by the subsequent electrocyclic ring opening of the cyclobutene moiety.

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