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Formation of Arenes via Diallylarenes: Strategic Utilization of Suzuki–Miyaura Cross‐Coupling, Claisen Rearrangement and Ring‐Closing Metathesis
Author(s) -
Kotha Sambasivarao,
Shah Vrajesh R.,
Mandal Kalyaneswar
Publication year - 2007
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.200600469
Subject(s) - chemistry , claisen rearrangement , metathesis , ring closing metathesis , salt metathesis reaction , combinatorial chemistry , ring (chemistry) , stereochemistry , suzuki reaction , coupling (piping) , organic chemistry , catalysis , palladium , polymerization , mechanical engineering , polymer , engineering
Two new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki–Miyaura cross‐coupling reaction. To this end, various ortho‐ diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring‐closing metathesis (RCM) and one‐pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2‐substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.