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Catalytic Generation of Arynes and Trapping by Nucleophilic Addition and Iodination
Author(s) -
Hamura Toshiyuki,
Chuda Yu,
Nakatsuji Yuya,
Suzuki Keisuke
Publication year - 2012
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/anie.201108415
Subject(s) - aryne , nucleophile , chemistry , catalysis , stoichiometry , halogenation , iodine , lithium (medication) , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , endocrinology
A fair exchange : In the title reaction, alkynyllithium serves as an initiator for benzyne generation through an iodine–lithium exchange (see scheme; Tf=trifluoromethanesulfonyl). When performed in the presence of stoichiometric amounts of a nucleophile, the generated benzyne undergoes attack by lithio nucleophiles to generate aryllithium, which is then iodinated by iodoalkyne to give the iodoarenes 1 .
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