Stepwise delivery of two methoxy groups of arylaldehyde acetals across the phenyl ring. Vacant site-controlled palladium catalysis

Itaru Nakamura; Yuya Mizushima; Ilya Gridnev; Yoshinori Yamamoto

doi:10.1021/ja051114j

Stepwise delivery of two methoxy groups of arylaldehyde acetals across the phenyl ring. Vacant site-controlled palladium catalysis

Itaru Nakamura, Yuya Mizushima, Ilya Gridnev, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

A new catalytic cyclization of o-alkynylbenzaldehyde acetals 1 to the functionalized indenes 2 was found to be strictly controlled by the number of triphenylphosphine ligands on the Pd catalyst. Only complexes with three available coordination sites on Pd catalyze this reaction. Mechanistic study suggests that π-coordination of Pd to the benzene ring is a key step controlled by the number of vacant coordination sites.

Original language	English
Pages (from-to)	9844-9847
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	127
Issue number	27
DOIs	https://doi.org/10.1021/ja051114j
Publication status	Published - 2005 Jul 13
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja051114j

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abstract = "A new catalytic cyclization of o-alkynylbenzaldehyde acetals 1 to the functionalized indenes 2 was found to be strictly controlled by the number of triphenylphosphine ligands on the Pd catalyst. Only complexes with three available coordination sites on Pd catalyze this reaction. Mechanistic study suggests that π-coordination of Pd to the benzene ring is a key step controlled by the number of vacant coordination sites.",

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AU - Gridnev, Ilya

AU - Yamamoto, Yoshinori

PY - 2005/7/13

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AB - A new catalytic cyclization of o-alkynylbenzaldehyde acetals 1 to the functionalized indenes 2 was found to be strictly controlled by the number of triphenylphosphine ligands on the Pd catalyst. Only complexes with three available coordination sites on Pd catalyze this reaction. Mechanistic study suggests that π-coordination of Pd to the benzene ring is a key step controlled by the number of vacant coordination sites.

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Stepwise delivery of two methoxy groups of arylaldehyde acetals across the phenyl ring. Vacant site-controlled palladium catalysis

Abstract

ASJC Scopus subject areas

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