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Titanocene‐Catalyzed Regioselective Alkylation of Styrenes with Grignard Reagents Using β‐Bromoethyl Ethers, Thioethers, or Amines
Author(s) -
Terao Jun,
Kato Yuichiro,
Kambe Nobuaki
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800134
Subject(s) - alkylation , regioselectivity , chemistry , alkyl , catalysis , reagent , ether , heteroatom , organic chemistry , medicinal chemistry , solvent
Regioselective double alkylation of styrenes with alkyl Grignard reagents and alkyl bromides having a heteroatom functional group at the β‐position has been achieved by the use of a titanocene catalyst in THF. When ether was used instead of THF as a solvent, monoalkylation by substitution of a vinylic hydrogen atom with an alkyl group proceeded under similar conditions. These reactions involve the addition of alkyl radicals to styrenes to form benzylic radical intermediates.