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Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis

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Title Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis
 
Creator KOTHA, S
SHAH, VR
MANDAL, K
 
Subject surface-mediated reactions
allyl vinyl ethers
olefin-metathesis
benzannulation reaction
aromatic-compounds
organic-synthesis
phenol oxidation
anthracyclinones
benzoannulation
heterocycles
benzoannulation
claisen rearrangement
diallylarenes
2-naphthalene derivatives
ring-closing metathesis
suzuki-miyaura cross-coupling
 
Description 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.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2011-09-01T16:57:30Z
2011-12-26T12:59:44Z
2011-12-27T05:52:28Z
2011-09-01T16:57:30Z
2011-12-26T12:59:44Z
2011-12-27T05:52:28Z
2007
 
Type Article
 
Identifier ADVANCED SYNTHESIS & CATALYSIS, 349(7), 1159-1172
1615-4150
http://dx.doi.org/10.1002/adsc.200600469
http://dspace.library.iitb.ac.in/xmlui/handle/10054/12826
http://hdl.handle.net/10054/12826
 
Language en