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

Vladimir Gevorgyan; Long Guo Quan; Yoshinori Yamamoto

doi:10.1016/S0040-4039(99)00656-5

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

Vladimir Gevorgyan, Long Guo Quan, Yoshinori Yamamoto

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144 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4089-4092
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(99)00656-5
State	Published - May 21 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes",

abstract = "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.",

author = "Vladimir Gevorgyan and Quan, {Long Guo} and Yoshinori Yamamoto",

year = "1999",

month = may,

day = "21",

doi = "10.1016/S0040-4039(99)00656-5",

language = "English (US)",

volume = "40",

pages = "4089--4092",

journal = "Tetrahedron Letters",

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T1 - Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes

AU - Gevorgyan, Vladimir

AU - Quan, Long Guo

AU - Yamamoto, Yoshinori

PY - 1999/5/21

Y1 - 1999/5/21

N2 - 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.

AB - 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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U2 - 10.1016/S0040-4039(99)00656-5

DO - 10.1016/S0040-4039(99)00656-5

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

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

Abstract

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