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Cyclopropanation of Benzene Rings by Oxidatively Generated α‐Oxo Gold Carbene: One‐Pot Access to Tetrahydropyranone‐Fused Cycloheptatrienes from Propargyl Benzyl Ethers
Author(s) -
Ji Kegong,
Zhang Liming
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701322
Subject(s) - cyclopropanation , cyclopropane , chemistry , propargyl , isomerization , cycloheptatriene , carbene , benzene , medicinal chemistry , oxidative addition , ring (chemistry) , catalysis , organic chemistry
Cyclopropanations of benzene rings by oxidatively generated α‐oxo gold carbenes are for the first time demonstrated in a Buchner reaction, in which readily available propargyl benzyl ethers are converted in one‐pot to tetrahydropyranone‐fused cycloheptatrienes via sequential oxidative gold catalysis and base‐promoted isomerization. Additional examples of arene cyclopropanations without fragmentation of the cyclopropane ring are also realized.