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½ð³æ (СÓÐÃûÆø)


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The same research group developed two different
protocols for the preparation of 2-substituted-3-
allylbenzofurans from o-alkynylphenols and allyl
carbonates under palladium catalysis ¡£
The stepwise method (method A) was based on the
preparation of stereo- and regioisomeric mixtures of
O-allyl derivatives and their subsequent cyclization
to benzofurans, being the method of choice when
steric differences between the two allylic termini are
small. The one-pot protocol (method B), omitting
isolation of the O-allyl derivatives, was employed
when the reaction proceeds through ¨¨3-allylpalladium
complexes and also when the two allylic termini are
markedly different from a steric point of view.
Concerning the reaction mechanism, the cyclization
of the O-allyl derivatives was suggested to proceed
through the palladium-promoted ionization of the
allylic C-O bond and displacement of one ligand to
the palladium by the carbon-carbon triple bond,
intramolecular nucleophilic attack of the oxygen atom
across the activated carbon-carbon triple bond, and
reductive elimination ¡£

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½ð³æ (СÓÐÃûÆø)


ÒýÓûØÌû:
Originally posted by 8814402 at 2011-02-20 11:31:49:
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3Â¥2011-02-20 19:54:34
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The same research group developed two different protocols for the preparation of 2-substituted-3-allylbenzofurans from o-alkynylphenols and allyl carbonates under palladium catalysis.

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4Â¥2011-02-20 22:46:09
ÒÑÔÄ   »Ø¸´´ËÂ¥   ¹Ø×¢TA ¸øTA·¢ÏûÏ¢ ËÍTAºì»¨ TAµÄ»ØÌû
answerball(½ð±Ò+1, ·­ÒëEPI+1): 2011-02-21 16:05:23

The stepwise method (method A) was based on the
preparation of stereo- and regioisomeric mixtures of
O-allyl derivatives and their subsequent cyclization
to benzofurans, being the method of choice when
steric differences between the two allylic termini are
small.
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