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Three‐Component Coupling Reactions of Alkyl Iodides, 1,3‐Dienes, and Carbonyl Compounds by Sequential Generation of Radical and Anionic Species with CrCl 2
Author(s) -
Takai Kazuhiko,
Matsukawa Naoto,
Takahashi Akira,
Fujii Takafumi
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980202)37:1/2<152::aid-anie152>3.0.co;2-8
Subject(s) - allylic rearrangement , chemistry , radical , alkyl , aldehyde , medicinal chemistry , diene , chloride , chromium , coupling reaction , beta hydride elimination , intermolecular force , organic chemistry , photochemistry , polymer chemistry , catalysis , molecule , natural rubber
The mild reductant chromium( II ) chloride can discriminate between alkyl iodides, alkyl radicals, and allylic radicals. In the presence of Cr II the alkyl radical is so long‐lived that it can undergo intermolecular addition to a 1,3‐diene. Rapid one‐electron reduction of the formed allylic radical results in an allylic chromium( II ) species, which adds to an aldehyde to afford a three‐component coupling product [see, for example, Eq. (a)].