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Oxidative Coupling via Organocopper Compounds
Author(s) -
Kauffmann Thomas
Publication year - 1974
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197402911
Subject(s) - disproportionation , metalation , chemistry , hydrazine (antidepressant) , oxidative coupling of methane , derivative (finance) , coupling reaction , oxidative phosphorylation , combinatorial chemistry , oxidative addition , limiting , organic chemistry , catalysis , mechanical engineering , biochemistry , chromatography , financial economics , engineering , economics
The type of reaction described here, which achieved preparative importance before the turn of the century in the form of the Glaser reaction, has found new applications in recent years: Syntheses of 1,3‐dienes, 2,3,6,7‐tetraaza‐1,3,5,7‐tetraenes, 2,3‐diaza‐1,3‐dienes, hydrazine derivatives, bis(heteroallyl) compounds, hetarenes, polyhetarenes, cyclopolyarenes, protophanes, phanes, and heteraprotophanes. The reaction, which consists in the metalation of the starting substance followed by oxidative coupling of the metal derivative, merits special preparative interest when several successive coupling processes are possible ( e. g. polyyne, polyarene, cyclopolyarene, and protophane syntheses). The main factors limiting its applicability are the high thermal stability of some organic copper compounds and the disproportionation of the ligands that frequently occurs as a competing reaction. Selective asymmetric linkages are not generally possible by this method.