Premium
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.