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Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes

✍ Scribed by Vladimir Gevorgyan; Long Guo Quan; Yoshinori Yamamoto

Book ID: 104261439
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 157 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00656-5

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✦ Synopsis

o-Bromobenzaldehyde 1, in the presence of a palladium catalyst, smoothly underwent consecutive intermolecular carbopalladation with internal alkynes 2 and then intramolecular nucleophilic vinylpalladation of the aldehyde function to produce the indenol derivatives 4 in high yields. Further heating of 4 under more elevated temperature caused complete isomerization to the corresponding indanones 8. A mechanism for this nucleophilic vinylpalladation of aromatic aldehydes is proposed.

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